DE2505267A1 - Digoxinderivate - Google Patents
DigoxinderivateInfo
- Publication number
- DE2505267A1 DE2505267A1 DE19752505267 DE2505267A DE2505267A1 DE 2505267 A1 DE2505267 A1 DE 2505267A1 DE 19752505267 DE19752505267 DE 19752505267 DE 2505267 A DE2505267 A DE 2505267A DE 2505267 A1 DE2505267 A1 DE 2505267A1
- Authority
- DE
- Germany
- Prior art keywords
- digoxin
- derivative
- reacting
- structural formula
- nan
- 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- Withdrawn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
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical class C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 title claims description 35
- 229960005156 digoxin Drugs 0.000 claims description 22
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 claims description 19
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 5
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 3
- MYTOTTSMVMWVJN-STQMWFEESA-N Lys-Tyr Chemical compound NCCCC[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 MYTOTTSMVMWVJN-STQMWFEESA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 238000011088 calibration curve Methods 0.000 description 5
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 229910052722 tritium Inorganic materials 0.000 description 4
- -1 BOC- Chemical class 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000002372 labelling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000984 immunochemical effect Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- SHIBSTMRCDJXLN-UHFFFAOYSA-N Digoxigenin Natural products C1CC(C2C(C3(C)CCC(O)CC3CC2)CC2O)(O)C2(C)C1C1=CC(=O)OC1 SHIBSTMRCDJXLN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- 150000008575 L-amino acids Chemical group 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- QONQRTHLHBTMGP-UHFFFAOYSA-N digitoxigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C1=CC(=O)OC1 QONQRTHLHBTMGP-UHFFFAOYSA-N 0.000 description 1
- WDJUZGPOPHTGOT-XUDUSOBPSA-N digitoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O WDJUZGPOPHTGOT-XUDUSOBPSA-N 0.000 description 1
- SHIBSTMRCDJXLN-KCZCNTNESA-N digoxigenin Chemical compound C1([C@@H]2[C@@]3([C@@](CC2)(O)[C@H]2[C@@H]([C@@]4(C)CC[C@H](O)C[C@H]4CC2)C[C@H]3O)C)=CC(=O)OC1 SHIBSTMRCDJXLN-KCZCNTNESA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- MWZPENIJLUWBSY-VIFPVBQESA-N methyl L-tyrosinate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-VIFPVBQESA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-M periodate Chemical compound [O-]I(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-M 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US447249A US3925355A (en) | 1974-03-01 | 1974-03-01 | Labelled digoxin derivatives for radioimmunoassay |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2505267A1 true DE2505267A1 (de) | 1975-09-04 |
Family
ID=23775584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752505267 Withdrawn DE2505267A1 (de) | 1974-03-01 | 1975-02-07 | Digoxinderivate |
Country Status (6)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4184037A (en) * | 1973-06-21 | 1980-01-15 | Burroughs Wellcome Co. | Digoxin oxidized product |
| GB1471755A (en) * | 1974-06-20 | 1977-04-27 | Radiochemical Centre Ltd | Derivatives of digoxin and digotoxin |
| US4064227A (en) * | 1975-03-17 | 1977-12-20 | Mallinckrodt, Inc. | Radioimmunoassay method for the determination of cardiotonic glycosides |
| US4336185A (en) * | 1976-03-02 | 1982-06-22 | Rohm And Haas Company | Folic acid derivatives |
| US4056608A (en) * | 1976-04-08 | 1977-11-01 | Syva Company | Cardiac glycoside or aglycone assays |
| US4202874A (en) * | 1976-09-29 | 1980-05-13 | Becton Dickinson & Company | Monoradioiodinated derivatives and precursors for production thereon |
| US4221725A (en) * | 1977-08-12 | 1980-09-09 | E. R. Squibb & Sons, Inc. | Steroid derivatives and their use in radioimmunoassays |
| US4230621A (en) * | 1978-05-01 | 1980-10-28 | E. R. Squibb & Sons, Inc. | Steroid derivatives and their use in radioimmunoassays |
| US4345096A (en) * | 1979-01-17 | 1982-08-17 | E. R. Squibb & Sons, Inc. | Steroid derivatives and their use in radioimmunoassays |
| US4595656A (en) * | 1984-01-06 | 1986-06-17 | Becton Dickinson & Company | Coupling agents and products produced therefrom |
| US4670406A (en) * | 1984-01-06 | 1987-06-02 | Becton Dickinson And Company | Tracers for use in assays |
| US5104637A (en) * | 1985-02-06 | 1992-04-14 | University Of Cincinnati | Radio labeled dihematophorphyrin ether and its use in detecting and treating neoplastic tissue |
| DE3802060A1 (de) * | 1988-01-25 | 1989-07-27 | Boehringer Mannheim Gmbh | Hapten-protein-konjugate und ihre verwendung |
| DE3836656A1 (de) * | 1988-10-27 | 1990-05-03 | Boehringer Mannheim Gmbh | Neue digoxigenin-derivate und ihre verwendung |
| FR2836996A1 (fr) * | 2002-03-05 | 2003-09-12 | Centre Nat Rech Scient | PRECURSEURS DE TRACEURS IMMUNOLOGIQUES NON-PEPTIDIQUES COMPRENANT UN MOTIF TYROSYL-(X)n-LYSINE-(X)n-TYROSINE, PROCEDE DE PREPARATION ET LEURS APPLICATIONS |
| GB0228936D0 (en) * | 2002-12-12 | 2003-01-15 | Bio Med Reagents Ltd | "Labelled compounds |
| WO2015029035A1 (en) | 2013-08-29 | 2015-03-05 | Yeda Research And Development Co. Ltd. | SELECTIVE INHIBITORS OF α2 ISOFORM OF Na,K-ATPase AND USE FOR REDUCTION OF INTRA-OCULAR PRESSURE |
| WO2017013637A1 (en) * | 2015-07-19 | 2017-01-26 | Yeda Research And Development Co. Ltd. | Selective inhibitors of alpha2-containing isoforms of na,k-atpase and use thereof for reduction of intraocular pressure |
| US10668094B2 (en) | 2015-07-19 | 2020-06-02 | Yeda Research And Development Co. Ltd. | Selective inhibitors of Alpha2-containing isoforms of Na,K-ATPase and use thereof for reduction of intraocular pressure |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2885394A (en) * | 1956-12-11 | 1959-05-05 | Lasdon Foundation Inc | Modified saccharide compounds |
| US3014026A (en) * | 1958-09-05 | 1961-12-19 | Kroll Harry | Chelates of monosaccharide-amino acids and related compounds |
-
1974
- 1974-03-01 US US447249A patent/US3925355A/en not_active Expired - Lifetime
-
1975
- 1975-02-07 DE DE19752505267 patent/DE2505267A1/de not_active Withdrawn
- 1975-02-26 GB GB800775A patent/GB1453583A/en not_active Expired
- 1975-02-27 FR FR7506110A patent/FR2262670B1/fr not_active Expired
- 1975-02-27 JP JP50024478A patent/JPS50117766A/ja active Pending
- 1975-02-28 CA CA221,002A patent/CA1051870A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1453583A (en) | 1976-10-27 |
| FR2262670B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-04-21 |
| CA1051870A (en) | 1979-04-03 |
| US3925355A (en) | 1975-12-09 |
| JPS50117766A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-16 |
| FR2262670A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: HERZFELD, A., RECHTSANW., 6370 OBERURSEL |
|
| 8130 | Withdrawal |