DE2522224C3 - Jodierte Cholesterin-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltendes Mittel - Google Patents
Jodierte Cholesterin-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltendes MittelInfo
- Publication number
- DE2522224C3 DE2522224C3 DE2522224A DE2522224A DE2522224C3 DE 2522224 C3 DE2522224 C3 DE 2522224C3 DE 2522224 A DE2522224 A DE 2522224A DE 2522224 A DE2522224 A DE 2522224A DE 2522224 C3 DE2522224 C3 DE 2522224C3
- Authority
- DE
- Germany
- Prior art keywords
- ncl
- iodine
- compound
- radioactive
- ether
- 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
- 239000000203 mixture Substances 0.000 title description 27
- 238000000034 method Methods 0.000 title description 14
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001841 cholesterols Chemical class 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 27
- 230000002285 radioactive effect Effects 0.000 description 26
- 229910052740 iodine Inorganic materials 0.000 description 25
- 239000011630 iodine Substances 0.000 description 25
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 210000004100 adrenal gland Anatomy 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- -1 sulfonyloxy group Chemical group 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 4
- MHANIWWTVNYQGT-GUODMVMDSA-N [(3s,8s,9s,10s,13r,14s,17r)-3-hydroxy-13-methyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl]methyl 4-methylbenzenesulfonate Chemical compound C([C@]12CC[C@H](O)CC1=CC[C@H]1[C@@H]3CC[C@@H]([C@]3(CC[C@@H]12)C)[C@H](C)CCCC(C)C)OS(=O)(=O)C1=CC=C(C)C=C1 MHANIWWTVNYQGT-GUODMVMDSA-N 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 229940107816 ammonium iodide Drugs 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011734 sodium Substances 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical group [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000001919 adrenal effect Effects 0.000 description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- FIOAEFCJGZJUPW-FTLVODPJSA-N 19-iodocholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(CI)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 FIOAEFCJGZJUPW-FTLVODPJSA-N 0.000 description 1
- 101100006501 Caenorhabditis elegans cks-1 gene Proteins 0.000 description 1
- 208000014311 Cushing syndrome Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101100226146 Drosophila mojavensis Est-5 gene Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- LNMZTFKTLLGKFZ-MLGNXSNUSA-N [(3S,8S,9S,10R,13S,14S,17R)-10-hexyl-3-hydroxy-13-methyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl] benzenesulfonate Chemical compound C([C@H]1[C@@H]2CC=C3C[C@@H](O)CC[C@@]3([C@H]2CC[C@]1(C)[C@H]1[C@H](C)CCCC(C)C)CCCCCC)C1OS(=O)(=O)C1=CC=CC=C1 LNMZTFKTLLGKFZ-MLGNXSNUSA-N 0.000 description 1
- JTGBSSUVHACVSG-PXNILNIRSA-N [(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-13-methyl-17-[(2R)-6-methylheptan-2-yl]-10-propyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl] benzenesulfonate Chemical compound C([C@H]1[C@@H]2CC=C3C[C@@H](O)CC[C@@]3([C@H]2CC[C@]1(C)[C@H]1[C@H](C)CCCC(C)C)CCC)C1OS(=O)(=O)C1=CC=CC=C1 JTGBSSUVHACVSG-PXNILNIRSA-N 0.000 description 1
- PMCNCHYDBHAFGV-SGPYZGDTSA-N [(3s,8s,9s,10s,13r,14s,17r)-3-hydroxy-13-methyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl]methyl benzenesulfonate Chemical compound C([C@]12CC[C@H](O)CC1=CC[C@H]1[C@@H]3CC[C@@H]([C@]3(CC[C@@H]12)C)[C@H](C)CCCC(C)C)OS(=O)(=O)C1=CC=CC=C1 PMCNCHYDBHAFGV-SGPYZGDTSA-N 0.000 description 1
- PSXZZPFWHBADDF-TURLQYGPSA-N [(3s,8s,9s,10s,13r,14s,17r)-3-hydroxy-13-methyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl]methyl methanesulfonate Chemical compound C1C=C2C[C@@H](O)CC[C@]2(COS(C)(=O)=O)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 PSXZZPFWHBADDF-TURLQYGPSA-N 0.000 description 1
- STVUQIOTKNSZKO-RGKQOXAKSA-N [(3s,8s,9s,10s,13r,14s,17r)-3-hydroxy-13-methyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-10-yl]methyl pentane-1-sulfonate Chemical compound C1C[C@@H]2[C@](CC[C@H](O)C3)(COS(=O)(=O)CCCCC)C3=CC[C@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@]21C STVUQIOTKNSZKO-RGKQOXAKSA-N 0.000 description 1
- 210000004404 adrenal cortex Anatomy 0.000 description 1
- 208000020990 adrenal cortex carcinoma Diseases 0.000 description 1
- 208000007128 adrenocortical carcinoma Diseases 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 238000002601 radiography Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49056822A JPS511457A (en) | 1974-05-20 | 1974-05-20 | 6beetaaa yoodomechiru 199 noru 5 * 10 * koresuten 3beetaaa oorunoseizoho |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2522224A1 DE2522224A1 (de) | 1975-12-04 |
| DE2522224B2 DE2522224B2 (de) | 1978-06-08 |
| DE2522224C3 true DE2522224C3 (de) | 1979-02-22 |
Family
ID=13038053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2522224A Expired DE2522224C3 (de) | 1974-05-20 | 1975-05-20 | Jodierte Cholesterin-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltendes Mittel |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4075334A (enExample) |
| JP (1) | JPS511457A (enExample) |
| AU (1) | AU477030B2 (enExample) |
| DE (1) | DE2522224C3 (enExample) |
| FR (1) | FR2271834B1 (enExample) |
| GB (1) | GB1508023A (enExample) |
| NL (1) | NL162915C (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1550832A (en) * | 1975-07-02 | 1979-08-22 | Radiochemical Centre Ltd | Selenium-containing steroids and their use in organ visualisation |
| WO2008069890A2 (en) * | 2006-11-09 | 2008-06-12 | Thomas Jefferson University | Adrenal grk2 activity as a therapeutic target for heart failure |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3784576A (en) * | 1970-09-24 | 1974-01-08 | Univ Michigan | Halogenated cholesterol |
-
1974
- 1974-05-20 JP JP49056822A patent/JPS511457A/ja active Granted
-
1975
- 1975-03-27 US US05/562,666 patent/US4075334A/en not_active Expired - Lifetime
- 1975-05-15 GB GB20572/75A patent/GB1508023A/en not_active Expired
- 1975-05-16 NL NL7505787.A patent/NL162915C/xx not_active IP Right Cessation
- 1975-05-19 AU AU81275/75A patent/AU477030B2/en not_active Expired
- 1975-05-20 DE DE2522224A patent/DE2522224C3/de not_active Expired
- 1975-05-20 FR FR7515659A patent/FR2271834B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7505787A (nl) | 1975-11-24 |
| JPS538696B2 (enExample) | 1978-03-31 |
| AU8127575A (en) | 1976-10-14 |
| US4075334A (en) | 1978-02-21 |
| JPS511457A (en) | 1976-01-08 |
| AU477030B2 (en) | 1976-10-14 |
| GB1508023A (en) | 1978-04-19 |
| DE2522224B2 (de) | 1978-06-08 |
| NL162915C (nl) | 1980-07-15 |
| FR2271834B1 (enExample) | 1978-11-10 |
| NL162915B (nl) | 1980-02-15 |
| DE2522224A1 (de) | 1975-12-04 |
| FR2271834A1 (enExample) | 1975-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |