FR2414515A1 - Tritium labelled estradienone(s) useful as diagnostic agents - esp. for detecting androgenic receptors in tumours - Google Patents
Tritium labelled estradienone(s) useful as diagnostic agents - esp. for detecting androgenic receptors in tumoursInfo
- Publication number
- FR2414515A1 FR2414515A1 FR7800659A FR7800659A FR2414515A1 FR 2414515 A1 FR2414515 A1 FR 2414515A1 FR 7800659 A FR7800659 A FR 7800659A FR 7800659 A FR7800659 A FR 7800659A FR 2414515 A1 FR2414515 A1 FR 2414515A1
- Authority
- FR
- France
- Prior art keywords
- beta
- estra
- give
- cyclic
- tritium
- 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.)
- Granted
Links
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 title abstract 3
- 229910052722 tritium Inorganic materials 0.000 title abstract 3
- 206010028980 Neoplasm Diseases 0.000 title 1
- 230000001548 androgenic effect Effects 0.000 title 1
- 229940039227 diagnostic agent Drugs 0.000 title 1
- 239000000032 diagnostic agent Substances 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 abstract 1
- 238000006027 Birch reduction reaction Methods 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 abstract 1
- CCVTXCCLDMZLFS-BDXSIMOUSA-N [(8R,9S,13R,14S)-1,4,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-13-yl]methanol Chemical compound OC[C@@]12CCC[C@H]1[C@@H]1CCC=3CC=CCC3[C@H]1CC2 CCVTXCCLDMZLFS-BDXSIMOUSA-N 0.000 abstract 1
- VQHQLBARMFAKSV-AANPDWTMSA-N [(8r,9s,13s,14s,17s)-3-acetyloxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1CC2=CC(OC(C)=O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)C)[C@@]1(C)CC2 VQHQLBARMFAKSV-AANPDWTMSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- CMXKUJNZWYTFJN-XFUVECHXSA-N bolandiol Chemical compound O[C@H]1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 CMXKUJNZWYTFJN-XFUVECHXSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
Tritiumllabelled steroids of formula (I) are new. (where T = tritium; Z = a blocked ketonic grp. which is a cyclic or non-cyclic ketal, thioketal, or mixed ketal, the cyclic bridges contg. 2-4C and the non-cyclic bridges contg. 1 or 2 C). (I) are prepd. by the following route: 3,17-beta - diacetoxy estra-1,3,5(10) 6-tetraene (II) is reduced by tritium in the presence of a catalyst, partic. palladium hydroxide to give 3, 17 beta-diacetoxy estra-1,3,5(10) triene 6,7-T2 (III). This is saponified with a strong base to give 3, 17 beta-dihydroxy-estra 1,3,5(10) triene 6,7-T2 (IV). The 3-OH grp. is alkylated, such as with dimethyl sulphate and the prod. undergoes a Birch reaction by the action of lithium in ammonia, to give 3-OR -17 beta hydroxyestra 2,5(10) diene 6,7-T2 (V) (where R = 1-4 C Alkyl) Treatment with weak acid gives 3-oxo 17 beta-hydroxy 5(10) estren 6,7-T2 (VI). This is treated with pyridinium perbromide to give 3-oxo-17 beta -hydroxy estra-4,9-diene 6,7-T2 (VII). This prod. is oxidised with aq. sulphochromic soln., and the 3-ketone gp. is ketalised.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7800659A FR2414515A1 (en) | 1978-01-11 | 1978-01-11 | Tritium labelled estradienone(s) useful as diagnostic agents - esp. for detecting androgenic receptors in tumours |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7800659A FR2414515A1 (en) | 1978-01-11 | 1978-01-11 | Tritium labelled estradienone(s) useful as diagnostic agents - esp. for detecting androgenic receptors in tumours |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2414515A1 true FR2414515A1 (en) | 1979-08-10 |
| FR2414515B1 FR2414515B1 (en) | 1981-08-07 |
Family
ID=9203315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7800659A Granted FR2414515A1 (en) | 1978-01-11 | 1978-01-11 | Tritium labelled estradienone(s) useful as diagnostic agents - esp. for detecting androgenic receptors in tumours |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2414515A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2549067A1 (en) * | 1983-06-14 | 1985-01-18 | Roussel Uclaf | TRITIUM-labeled RADIOACTIVE ESTRADIAN DERIVATIVES, PROCESS FOR THE PREPARATION THEREOF AND THEIR USE FOR THE STUDY AND RADIATION IMMUNOLOGICAL DETERMINATION OF STEROIDS IN BIOLOGICAL FLUIDS |
-
1978
- 1978-01-11 FR FR7800659A patent/FR2414515A1/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2549067A1 (en) * | 1983-06-14 | 1985-01-18 | Roussel Uclaf | TRITIUM-labeled RADIOACTIVE ESTRADIAN DERIVATIVES, PROCESS FOR THE PREPARATION THEREOF AND THEIR USE FOR THE STUDY AND RADIATION IMMUNOLOGICAL DETERMINATION OF STEROIDS IN BIOLOGICAL FLUIDS |
| EP0135400A2 (en) * | 1983-06-14 | 1985-03-27 | Roussel-Uclaf | Estradiene derivatives labelled with tritium, their preparation and intermediates for their preparation, and their utilization in the study and in the determination of steroids in biological fluids |
| EP0135400A3 (en) * | 1983-06-14 | 1985-08-14 | Roussel-Uclaf | Estradiene derivatives labelled with tritium, their preparation and intermediates for their preparation, and their utilization in the study and in the determination of steroids in biological fluids |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2414515B1 (en) | 1981-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |