DE2145282C3 - 1-(Jodhydroxyphenyl)-2-aminopropanderivate, Verfahren zu ihrer Herstellung und diagnostisches Mittel - Google Patents
1-(Jodhydroxyphenyl)-2-aminopropanderivate, Verfahren zu ihrer Herstellung und diagnostisches MittelInfo
- Publication number
- DE2145282C3 DE2145282C3 DE19712145282 DE2145282A DE2145282C3 DE 2145282 C3 DE2145282 C3 DE 2145282C3 DE 19712145282 DE19712145282 DE 19712145282 DE 2145282 A DE2145282 A DE 2145282A DE 2145282 C3 DE2145282 C3 DE 2145282C3
- Authority
- DE
- Germany
- Prior art keywords
- iodine
- hydrogen
- radioactive
- organs
- substituents
- 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
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims 2
- ZAQUCKDACBPPCZ-UHFFFAOYSA-N 2-(2-aminopropyl)-6-iodophenol Chemical class CC(N)CC1=CC=CC(I)=C1O ZAQUCKDACBPPCZ-UHFFFAOYSA-N 0.000 title 1
- 229940039227 diagnostic agent Drugs 0.000 title 1
- 239000000032 diagnostic agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052740 iodine Inorganic materials 0.000 claims description 26
- 239000011630 iodine Substances 0.000 claims description 23
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 18
- 210000000056 organ Anatomy 0.000 claims description 15
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 14
- 230000002285 radioactive effect Effects 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 201000001441 melanoma Diseases 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 210000001943 adrenal medulla Anatomy 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 238000003745 diagnosis Methods 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 4
- 210000004100 adrenal gland Anatomy 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- XMBWDFGMSWQBCA-RNFDNDRNSA-M iodine-131(1-) Chemical compound [131I-] XMBWDFGMSWQBCA-RNFDNDRNSA-M 0.000 claims description 4
- 238000009825 accumulation Methods 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- -1 hydrogen phenylethylamine derivatives Chemical class 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000001919 adrenal effect Effects 0.000 claims description 2
- 238000002474 experimental method Methods 0.000 claims description 2
- 238000012360 testing method Methods 0.000 claims description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 claims 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 claims 1
- 241000272517 Anseriformes Species 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 150000003943 catecholamines Chemical class 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- 230000029142 excretion Effects 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- XMBWDFGMSWQBCA-YPZZEJLDSA-N iodane Chemical compound [125IH] XMBWDFGMSWQBCA-YPZZEJLDSA-N 0.000 claims 1
- 229940044173 iodine-125 Drugs 0.000 claims 1
- 238000002372 labelling Methods 0.000 claims 1
- 238000005259 measurement Methods 0.000 claims 1
- 230000000877 morphologic effect Effects 0.000 claims 1
- LCSPTLBPHFPXFQ-UHFFFAOYSA-N n,n-dihydroxy-2-phenylethanamine Chemical compound ON(O)CCC1=CC=CC=C1 LCSPTLBPHFPXFQ-UHFFFAOYSA-N 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 229960002748 norepinephrine Drugs 0.000 claims 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 1
- 238000009206 nuclear medicine Methods 0.000 claims 1
- 208000028591 pheochromocytoma Diseases 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 238000011160 research Methods 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
- 150000003667 tyrosine derivatives Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 6
- AXDLCFOOGCNDST-UHFFFAOYSA-N N-methyl-DL-tyrosine Natural products CNC(C(O)=O)CC1=CC=C(O)C=C1 AXDLCFOOGCNDST-UHFFFAOYSA-N 0.000 description 5
- 238000004816 paper chromatography Methods 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000006192 iodination reaction Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 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
- LPNCXXXBCCHJQI-UHFFFAOYSA-N 4-(2-aminopropyl)-2-iodophenol Chemical compound IC=1C=C(C=CC1O)CC(C)N LPNCXXXBCCHJQI-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007979 citrate buffer Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 2
- 230000026045 iodination Effects 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011146 sterile filtration Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- RDKJNZQKNORJDA-UHFFFAOYSA-N 4-(2-amino-1-hydroxypropyl)-2-iodophenol Chemical compound IC=1C=C(C=CC1O)C(C(C)N)O RDKJNZQKNORJDA-UHFFFAOYSA-N 0.000 description 1
- RZCJLMTXBMNRAD-UHFFFAOYSA-N 4-(2-aminopropyl)phenol;hydrobromide Chemical compound Br.CC(N)CC1=CC=C(O)C=C1 RZCJLMTXBMNRAD-UHFFFAOYSA-N 0.000 description 1
- VMLXUINOOLKVSK-UHFFFAOYSA-N 4-[1-hydroxy-2-(methylamino)propyl]-2-iodophenol Chemical compound IC=1C=C(C=CC1O)C(C(C)NC)O VMLXUINOOLKVSK-UHFFFAOYSA-N 0.000 description 1
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 description 1
- KLNYAAKKPOJQNJ-UHFFFAOYSA-N 5-(2-amino-1-hydroxypropyl)-2-iodophenol Chemical compound CC(N)C(O)C1=CC=C(I)C(O)=C1 KLNYAAKKPOJQNJ-UHFFFAOYSA-N 0.000 description 1
- PWSWICJHVYFHSV-UHFFFAOYSA-N CC(N)Cc1ccc(I)c(O)c1 Chemical compound CC(N)Cc1ccc(I)c(O)c1 PWSWICJHVYFHSV-UHFFFAOYSA-N 0.000 description 1
- XXHBNVBDFWTSGY-UHFFFAOYSA-N CNCC(C(C=C1)=CC(I)=C1O)O Chemical compound CNCC(C(C=C1)=CC(I)=C1O)O XXHBNVBDFWTSGY-UHFFFAOYSA-N 0.000 description 1
- PZXRGBVNEJHVMI-UHFFFAOYSA-N CNCC(C(C=C1)=CC(O)=C1I)O Chemical compound CNCC(C(C=C1)=CC(O)=C1I)O PZXRGBVNEJHVMI-UHFFFAOYSA-N 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 208000001382 Experimental Melanoma Diseases 0.000 description 1
- NHTGHBARYWONDQ-JTQLQIEISA-N L-α-methyl-Tyrosine Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-JTQLQIEISA-N 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CQDPDMJPVSAQFF-UHFFFAOYSA-N acetic acid;butan-2-ol Chemical compound CC(O)=O.CCC(C)O CQDPDMJPVSAQFF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000376 autoradiography Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 230000000684 melanotic effect Effects 0.000 description 1
- SSCFPXRLONNQFA-UHFFFAOYSA-N methanol;hydrate;hydrochloride Chemical compound O.Cl.OC SSCFPXRLONNQFA-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010405 reoxidation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000003462 vein Anatomy 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
-
- 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)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Investigating Or Analysing Biological Materials (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712145282 DE2145282C3 (de) | 1971-09-10 | 1971-09-10 | 1-(Jodhydroxyphenyl)-2-aminopropanderivate, Verfahren zu ihrer Herstellung und diagnostisches Mittel |
| NL7212061A NL7212061A (enExample) | 1971-09-10 | 1972-09-05 | |
| JP47090276A JPS4834845A (enExample) | 1971-09-10 | 1972-09-08 | |
| FR7232011A FR2154486B1 (enExample) | 1971-09-10 | 1972-09-08 | |
| AT774472A AT320617B (de) | 1971-09-10 | 1972-09-08 | Verfahren zur Herstellung von neuen radioaktiven 1-(Jodhydroxyphenyl)-alkanaminen |
| GB4216372A GB1391918A (en) | 1971-09-10 | 1972-09-11 | Iodohydroxyphenyl-aminoalkane derivatives and process for their manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712145282 DE2145282C3 (de) | 1971-09-10 | 1971-09-10 | 1-(Jodhydroxyphenyl)-2-aminopropanderivate, Verfahren zu ihrer Herstellung und diagnostisches Mittel |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2145282A1 DE2145282A1 (de) | 1973-03-22 |
| DE2145282B2 DE2145282B2 (de) | 1974-07-18 |
| DE2145282C3 true DE2145282C3 (de) | 1975-06-05 |
Family
ID=5819193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712145282 Expired DE2145282C3 (de) | 1971-09-10 | 1971-09-10 | 1-(Jodhydroxyphenyl)-2-aminopropanderivate, Verfahren zu ihrer Herstellung und diagnostisches Mittel |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4834845A (enExample) |
| AT (1) | AT320617B (enExample) |
| DE (1) | DE2145282C3 (enExample) |
| FR (1) | FR2154486B1 (enExample) |
| GB (1) | GB1391918A (enExample) |
| NL (1) | NL7212061A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3800302A1 (de) * | 1988-01-08 | 1989-07-27 | Kernforschungsanlage Juelich | Radiohalogentyrosinderivate, deren herstellung und verwendung |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0011858B1 (en) * | 1978-11-29 | 1983-05-18 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Radioiodine containing amines, their preparation and their use as brain imaging agents |
| DE69914748T2 (de) * | 1998-06-02 | 2004-12-02 | Dow Global Technologies, Inc., Midland | Radiojodierte phenole für brachytherapie |
-
1971
- 1971-09-10 DE DE19712145282 patent/DE2145282C3/de not_active Expired
-
1972
- 1972-09-05 NL NL7212061A patent/NL7212061A/xx unknown
- 1972-09-08 FR FR7232011A patent/FR2154486B1/fr not_active Expired
- 1972-09-08 AT AT774472A patent/AT320617B/de not_active IP Right Cessation
- 1972-09-08 JP JP47090276A patent/JPS4834845A/ja active Pending
- 1972-09-11 GB GB4216372A patent/GB1391918A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3800302A1 (de) * | 1988-01-08 | 1989-07-27 | Kernforschungsanlage Juelich | Radiohalogentyrosinderivate, deren herstellung und verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4834845A (enExample) | 1973-05-22 |
| DE2145282B2 (de) | 1974-07-18 |
| NL7212061A (enExample) | 1973-03-13 |
| FR2154486B1 (enExample) | 1976-03-05 |
| DE2145282A1 (de) | 1973-03-22 |
| GB1391918A (en) | 1975-04-23 |
| AT320617B (de) | 1975-02-25 |
| FR2154486A1 (enExample) | 1973-05-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE68928705T2 (de) | Technetium-99m-komplex zur untersuchung der nierenfunktion | |
| DE69131850T2 (de) | Technetium-99m-komplexe zur verwendung als radiopharmazeutische mittel | |
| DE3032781A1 (de) | Verfahren zur selektiven ablagerung einer radiopharmazeutischen verbindung in einem zielgewebe oder -organ und verbindungen zur durchfuehrung des verfahrens | |
| DE69116637T2 (de) | Mittel zur magnetischen Resonanzabbildung | |
| DE69426865T2 (de) | Pharmazeutische Zusammensetzungen enthaltend Pyryliumverbindungen, Pyryliumsalze und Verfahren zur Herstellung eines Medikaments enthaltend diese Verbindungen | |
| DE69617763T2 (de) | Radioaktives Kupferkomplex von Dithiosemicarbazonederivate oder Diaminediolschiffbasederivate | |
| DE69130982T2 (de) | Technetiumkomplex für die bestimmung der nierenfunktion | |
| CH644864A5 (de) | Psoralenderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate. | |
| DE3721206A1 (de) | Melatonin-derivate, ihre herstellung und sie enthaltende arzneimittel | |
| DE2145282C3 (de) | 1-(Jodhydroxyphenyl)-2-aminopropanderivate, Verfahren zu ihrer Herstellung und diagnostisches Mittel | |
| DE69718638T2 (de) | Tropanderivate insbesondere verwendbar zur detektion von dopamin transporters | |
| AT392469B (de) | Verfahren zur herstellung von neuen chinolinderivaten | |
| DE69706562T2 (de) | N-(4-acetyl-1-piperazinyl)-4-fluorobenzamidhydrat | |
| DE2034640C3 (de) | l-p-(7-Trifluormethyl-4-chinolyl) -amino-benzoyl-piperazine, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung von Bluthochdruck | |
| DE1934392C3 (de) | Neue 2-Pyridylthioamide und Verfahren zu ihrer Herstellung | |
| DE19519508C2 (de) | Radiohalogenierte Verbindungen und deren Verwendung zur Diagnose und Behandlung von Tumoren, insbesondere Melanomen | |
| DE1620177C3 (de) | N-(2-Hydroxyäthyl)-piperazinocarboxymethyl-tetracyclin, dessen pharmakologisch verwendbaren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2858813C2 (enExample) | ||
| DE2738131A1 (de) | Aminoketone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE2925345C2 (de) | N[β-(2-Mercaptoäthylcarbamoyl)-äthyl]-phenoxyalkansäureamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen | |
| CH652724A5 (de) | Pharmazeutisches praeparat, welches das glucuronid eines cytotoxischen aglycons enthaelt. | |
| DE69421173T2 (de) | Neue stickstoff-schwefel-liganden auf der basis eines heterocyclus für die verwendung in werkstoffen für die radiographische bildgebung | |
| DE905371C (de) | Verfahren zur Herstellung von neuen therapeutisch wirksamen quaternaeren Ammoniumsalzen | |
| DE2857555C3 (de) | Trans-4-palmitoylaminomethyl-cyclohexan-1-carbonsäure und deren Salze sowie dieselben enthaltendes Antitumormittel | |
| DE2430510B2 (de) | 16,17-Dihydroapovincaminsäureamide, Verfahren zu deren Herstellung und Arzneimittel, welche diese Verbindungen enthalten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |