NO133272B - - Google Patents
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- Publication number
- NO133272B NO133272B NO210870A NO210870A NO133272B NO 133272 B NO133272 B NO 133272B NO 210870 A NO210870 A NO 210870A NO 210870 A NO210870 A NO 210870A NO 133272 B NO133272 B NO 133272B
- Authority
- NO
- Norway
- Prior art keywords
- lithium
- reaction
- converted
- sodium
- selenomethionine
- Prior art date
Links
- 239000011669 selenium Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 13
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052711 selenium Inorganic materials 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 150000004694 iodide salts Chemical class 0.000 claims description 8
- WFXDZZWXRHZFGR-UHFFFAOYSA-N C[Se]C.[Li] Chemical compound C[Se]C.[Li] WFXDZZWXRHZFGR-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- VRDKYJSLDJDLML-UHFFFAOYSA-N methylselenol Chemical compound [Se]C VRDKYJSLDJDLML-UHFFFAOYSA-N 0.000 claims description 5
- MJEJPPQFUJAISK-UHFFFAOYSA-M sodium methaneselenolate Chemical compound [Na+].[Se-]C MJEJPPQFUJAISK-UHFFFAOYSA-M 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 claims description 2
- -1 lithium methyl selenide compound Chemical class 0.000 claims description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 description 6
- RJFAYQIBOAGBLC-UHFFFAOYSA-N Selenomethionine Natural products C[Se]CCC(N)C(O)=O RJFAYQIBOAGBLC-UHFFFAOYSA-N 0.000 description 6
- 229960002718 selenomethionine Drugs 0.000 description 6
- 230000002285 radioactive effect Effects 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- FBBCJQKVEYBQRP-UHFFFAOYSA-N 1-(2,2-dichloroethyl)piperazine-2,3-dione Chemical compound ClC(CN1C(C(NCC1)=O)=O)Cl FBBCJQKVEYBQRP-UHFFFAOYSA-N 0.000 description 2
- FCWKUKVVDABMQQ-UHFFFAOYSA-N 2-amino-4-benzylselanylbutanoic acid Chemical compound OC(=O)C(N)CC[Se]CC1=CC=CC=C1 FCWKUKVVDABMQQ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940080339 selenomethionine se 75 Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
- G21H—OBTAINING ENERGY FROM RADIOACTIVE SOURCES; APPLICATIONS OF RADIATION FROM RADIOACTIVE SOURCES, NOT OTHERWISE PROVIDED FOR; UTILISING COSMIC RADIATION
- G21H5/00—Applications of radiation from radioactive sources or arrangements therefor, not otherwise provided for
- G21H5/02—Applications of radiation from radioactive sources or arrangements therefor, not otherwise provided for as tracers
Landscapes
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- High Energy & Nuclear Physics (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6908609A NL163210C (nl) | 1969-06-06 | 1969-06-06 | Werkwijze voor de bereiding van radioactief seleno- methionine. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133272B true NO133272B (de) | 1975-12-29 |
| NO133272C NO133272C (de) | 1976-04-07 |
Family
ID=19807124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO210870A NO133272C (de) | 1969-06-06 | 1970-06-01 |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS4920184B1 (de) |
| AT (1) | AT303060B (de) |
| BE (1) | BE751531A (de) |
| CH (2) | CH546713A (de) |
| DE (1) | DE2065906C2 (de) |
| FR (1) | FR2052454A5 (de) |
| GB (1) | GB1281293A (de) |
| IT (1) | IT1004513B (de) |
| LU (1) | LU61068A1 (de) |
| NL (1) | NL163210C (de) |
| NO (1) | NO133272C (de) |
| SE (1) | SE373128B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4474746A (en) * | 1980-08-08 | 1984-10-02 | State University Of New York | Diagnostic radiopharmaceuticals for localization in target tissues exhibiting a regional pH shift relative to surrounding tissues |
| CA1236483A (en) * | 1984-03-19 | 1988-05-10 | Commonwealth Of Australia (The) | Labelling of organic molecules |
-
1969
- 1969-06-06 NL NL6908609A patent/NL163210C/xx not_active IP Right Cessation
-
1970
- 1970-05-28 FR FR7019520A patent/FR2052454A5/fr not_active Expired
- 1970-06-01 NO NO210870A patent/NO133272C/no unknown
- 1970-06-02 DE DE19702065906 patent/DE2065906C2/de not_active Expired
- 1970-06-03 IT IT6888570A patent/IT1004513B/it active
- 1970-06-03 JP JP4788270A patent/JPS4920184B1/ja active Pending
- 1970-06-04 SE SE779670A patent/SE373128B/xx unknown
- 1970-06-04 GB GB2701570A patent/GB1281293A/en not_active Expired
- 1970-06-05 CH CH850070A patent/CH546713A/de not_active IP Right Cessation
- 1970-06-05 BE BE751531D patent/BE751531A/xx unknown
- 1970-06-05 LU LU61068D patent/LU61068A1/xx unknown
- 1970-06-05 CH CH1385973A patent/CH549542A/de not_active IP Right Cessation
- 1970-06-08 AT AT512070A patent/AT303060B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2065906A1 (de) | 1977-01-20 |
| AT303060B (de) | 1972-11-10 |
| DE2026937B2 (de) | 1977-05-26 |
| GB1281293A (en) | 1972-07-12 |
| DE2065906C2 (de) | 1982-04-29 |
| IT1004513B (it) | 1976-07-20 |
| NL163210C (nl) | 1980-08-15 |
| NO133272C (de) | 1976-04-07 |
| BE751531A (fr) | 1970-12-07 |
| SE373128B (de) | 1975-01-27 |
| JPS4920184B1 (de) | 1974-05-23 |
| NL163210B (nl) | 1980-03-17 |
| CH546713A (de) | 1974-03-15 |
| LU61068A1 (de) | 1970-08-10 |
| CH549542A (de) | 1974-05-31 |
| NL6908609A (de) | 1970-12-08 |
| FR2052454A5 (de) | 1971-04-09 |
| DE2026937A1 (de) | 1970-12-17 |
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