GB1591357A - Preparation of directly iodinated steroid hormones and related directly halogenated compounds - Google Patents
Preparation of directly iodinated steroid hormones and related directly halogenated compounds Download PDFInfo
- Publication number
- GB1591357A GB1591357A GB39175/77A GB3917577A GB1591357A GB 1591357 A GB1591357 A GB 1591357A GB 39175/77 A GB39175/77 A GB 39175/77A GB 3917577 A GB3917577 A GB 3917577A GB 1591357 A GB1591357 A GB 1591357A
- Authority
- GB
- United Kingdom
- Prior art keywords
- steroid hormone
- halogenated
- parent
- radioactive
- steroid
- 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.)
- Expired
Links
- 239000003270 steroid hormone Substances 0.000 title claims description 68
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 title description 9
- 238000000034 method Methods 0.000 claims description 40
- 230000002285 radioactive effect Effects 0.000 claims description 35
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 150000003431 steroids Chemical class 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 23
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 claims description 20
- 229960001479 tosylchloramide sodium Drugs 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 10
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 10
- 150000008045 alkali metal halides Chemical class 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 8
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- PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 claims description 6
- QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
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- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 6
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- PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 claims description 3
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- ZESRJSPZRDMNHY-YFWFAHHUSA-N 11-deoxycorticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 ZESRJSPZRDMNHY-YFWFAHHUSA-N 0.000 claims description 3
- QGXBDMJGAMFCBF-BNSUEQOYSA-N 3alpha-hydroxy-5beta-androstan-17-one Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@@H]21 QGXBDMJGAMFCBF-BNSUEQOYSA-N 0.000 claims description 3
- QGXBDMJGAMFCBF-HLUDHZFRSA-N 5α-Androsterone Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-HLUDHZFRSA-N 0.000 claims description 3
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 claims description 3
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 3
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 3
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 claims description 3
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-AHCXROLUSA-N Iodine-123 Chemical compound [123I] ZCYVEMRRCGMTRW-AHCXROLUSA-N 0.000 claims description 3
- RZRPTBIGEANTGU-IRIMSJTPSA-N adrenosterone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 RZRPTBIGEANTGU-IRIMSJTPSA-N 0.000 claims description 3
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 claims description 3
- 229960005471 androstenedione Drugs 0.000 claims description 3
- AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 claims description 3
- 229940061641 androsterone Drugs 0.000 claims description 3
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 claims description 3
- 229960004544 cortisone Drugs 0.000 claims description 3
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 claims description 3
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 claims description 3
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- 229960003957 dexamethasone Drugs 0.000 claims description 3
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 3
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- XMBWDFGMSWQBCA-AKLPVKDBSA-N iodane Chemical compound [130IH] XMBWDFGMSWQBCA-AKLPVKDBSA-N 0.000 claims description 3
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- 229960002847 prasterone Drugs 0.000 claims description 3
- 229960000249 pregnenolone Drugs 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 230000002269 spontaneous effect Effects 0.000 claims description 3
- DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 claims 2
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- ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 claims 2
- JERGUCIJOXJXHF-TVWVXWENSA-N 17alpha-hydroxypregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 JERGUCIJOXJXHF-TVWVXWENSA-N 0.000 claims 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical class [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- FVAUCKIRQBBSSJ-VVUPZWBASA-M sodium;iodine-123(1-) Chemical compound [Na+].[123I-] FVAUCKIRQBBSSJ-VVUPZWBASA-M 0.000 description 1
- FVAUCKIRQBBSSJ-FXMLPJBTSA-M sodium;iodine-125(1-) Chemical compound [Na+].[125I-] FVAUCKIRQBBSSJ-FXMLPJBTSA-M 0.000 description 1
- FVAUCKIRQBBSSJ-LAIFMVDKSA-M sodium;iodine-131(1-) Chemical compound [Na+].[131I-] FVAUCKIRQBBSSJ-LAIFMVDKSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 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 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0493—Steroids, e.g. cholesterol, testosterone
-
- 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
- G01N33/74—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving hormones or other non-cytokine intercellular protein regulatory factors such as growth factors, including receptors to hormones and growth factors
- G01N33/743—Steroid hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Physics & Mathematics (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Urology & Nephrology (AREA)
- Cell Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Endocrinology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Food Science & Technology (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/727,284 US4321208A (en) | 1976-09-27 | 1976-09-27 | Preparation of directly iodinated steroid hormones and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1591357A true GB1591357A (en) | 1981-06-17 |
Family
ID=24922054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39175/77A Expired GB1591357A (en) | 1976-09-27 | 1977-09-19 | Preparation of directly iodinated steroid hormones and related directly halogenated compounds |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4321208A (enExample) |
| JP (1) | JPS53127453A (enExample) |
| CA (1) | CA1102305A (enExample) |
| DE (1) | DE2742903A1 (enExample) |
| FR (1) | FR2365587A1 (enExample) |
| GB (1) | GB1591357A (enExample) |
| IN (1) | IN146286B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4450149A (en) * | 1981-06-15 | 1984-05-22 | Research Corporation | Radiohalogenation method |
| DE3337179A1 (de) * | 1983-10-10 | 1985-05-23 | Schering AG, 1000 Berlin und 4709 Bergkamen | Estran- und androstan-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende praeparate |
| US4780420A (en) * | 1985-09-30 | 1988-10-25 | Yale University | Progesterone receptor ligands |
| IT1296576B1 (it) * | 1997-11-27 | 1999-07-14 | Promau Srl | Apparecchiatura automatica per la curvatura di lamiere, con controllo selettivo digitale |
| US7238338B1 (en) * | 2001-06-22 | 2007-07-03 | Triumf | System and method for the large scale labeling of compounds with radiohalogens |
| DE10141937A1 (de) * | 2001-08-28 | 2003-03-27 | Alfred Schmidt | Markierung der Aromatase |
| US8173983B1 (en) | 2010-01-07 | 2012-05-08 | Velayudhan Sahadevan | All field simultaneous radiation therapy |
| BRPI1101556A2 (pt) * | 2011-04-19 | 2015-07-14 | Univ Fed De Pernambuco Ufpe | Composto antitumoral testosterona - ( iodo radioativo) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953431A (en) * | 1971-05-24 | 1976-04-27 | Becton, Dickinson & Company | Derivatives of digoxigenin |
| GB1441253A (en) * | 1972-06-22 | 1976-06-30 | Wellcome Found | Reagents for the assay of cardiac glycosides |
| GB1441101A (en) * | 1972-06-22 | 1976-06-30 | Wellcome Found | Reagents for the assay of cardenolide glycosides and aglycones |
| DE2260933C3 (de) * | 1972-12-08 | 1981-08-20 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Verfahren zur Herstellung von durch radioaktives Halogen markierten organischen Verbindungen |
| US4013688A (en) * | 1972-12-20 | 1977-03-22 | The Upjohn Company | Radioimmunoassay agents |
-
1976
- 1976-09-27 US US05/727,284 patent/US4321208A/en not_active Expired - Lifetime
-
1977
- 1977-09-13 CA CA286,659A patent/CA1102305A/en not_active Expired
- 1977-09-19 GB GB39175/77A patent/GB1591357A/en not_active Expired
- 1977-09-23 DE DE19772742903 patent/DE2742903A1/de not_active Withdrawn
- 1977-09-26 FR FR7728950A patent/FR2365587A1/fr active Granted
- 1977-09-27 JP JP11525377A patent/JPS53127453A/ja active Pending
- 1977-09-27 IN IN1453/CAL/77A patent/IN146286B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4321208A (en) | 1982-03-23 |
| JPS53127453A (en) | 1978-11-07 |
| DE2742903A1 (de) | 1978-03-30 |
| FR2365587A1 (fr) | 1978-04-21 |
| IN146286B (enExample) | 1979-04-14 |
| FR2365587B3 (enExample) | 1980-07-11 |
| CA1102305A (en) | 1981-06-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |