CA1161455A - Method for the preparation of a scintillographic agent - Google Patents
Method for the preparation of a scintillographic agentInfo
- Publication number
- CA1161455A CA1161455A CA000325231A CA325231A CA1161455A CA 1161455 A CA1161455 A CA 1161455A CA 000325231 A CA000325231 A CA 000325231A CA 325231 A CA325231 A CA 325231A CA 1161455 A CA1161455 A CA 1161455A
- Authority
- CA
- Canada
- Prior art keywords
- solution
- acid
- water
- iminodiacetic acid
- derivative
- 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 abstract description 19
- 238000002360 preparation method Methods 0.000 title claims description 6
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 14
- SYSYYPWIRNXNQI-UHFFFAOYSA-N 2-[[2-amino-1-(2,4-dimethylphenyl)-2-oxoethyl]-(carboxymethyl)amino]acetic acid Chemical compound CC1=CC=C(C(N(CC(O)=O)CC(O)=O)C(N)=O)C(C)=C1 SYSYYPWIRNXNQI-UHFFFAOYSA-N 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 229960000443 hydrochloric acid Drugs 0.000 claims description 15
- 235000011167 hydrochloric acid Nutrition 0.000 claims description 15
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 11
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 11
- 239000001119 stannous chloride Substances 0.000 claims description 11
- 235000011150 stannous chloride Nutrition 0.000 claims description 11
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 239000013049 sediment Substances 0.000 claims description 6
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 5
- 150000008061 acetanilides Chemical class 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 238000001990 intravenous administration Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 4
- 229910052713 technetium Inorganic materials 0.000 claims description 4
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000008174 sterile solution Substances 0.000 claims description 3
- RISSLKJAGXQNAQ-UHFFFAOYSA-N 2-[carboxymethyl-[2-(2,4-dimethylanilino)-2-oxoethyl]amino]acetic acid Chemical compound CC1=CC=C(NC(=O)CN(CC(O)=O)CC(O)=O)C(C)=C1 RISSLKJAGXQNAQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 229940013123 stannous chloride Drugs 0.000 claims 5
- 239000003708 ampul Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- YICAMJWHIUMFDI-UHFFFAOYSA-N 4-acetamidotoluene Chemical compound CC(=O)NC1=CC=C(C)C=C1 YICAMJWHIUMFDI-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 1
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 abstract description 2
- 229940056501 technetium 99m Drugs 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 238000010992 reflux Methods 0.000 description 4
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
- VYZPXGMSAOCYOL-UHFFFAOYSA-N 2-[2-(2-aminoethyl)phenyl]ethanamine Chemical compound NCCC1=CC=CC=C1CCN VYZPXGMSAOCYOL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SNPZDXACCGIJNK-UHFFFAOYSA-N N-Acetyl-2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1NC(C)=O SNPZDXACCGIJNK-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0478—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group complexes from non-cyclic ligands, e.g. EDTA, MAG3
-
- 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)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1978205961A PL115524B1 (en) | 1978-04-10 | 1978-04-10 | Process for manufacturing scintigraphic agent |
| PL205961 | 1978-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1161455A true CA1161455A (en) | 1984-01-31 |
Family
ID=19988576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000325231A Expired CA1161455A (en) | 1978-04-10 | 1979-04-10 | Method for the preparation of a scintillographic agent |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4313926A (en, 2012) |
| BE (1) | BE875466A (en, 2012) |
| CA (1) | CA1161455A (en, 2012) |
| CH (1) | CH644763A5 (en, 2012) |
| DD (1) | DD142653A5 (en, 2012) |
| DE (1) | DE2913173A1 (en, 2012) |
| FR (1) | FR2422397A1 (en, 2012) |
| GB (1) | GB2018762B (en, 2012) |
| HU (1) | HU178782B (en, 2012) |
| IT (1) | IT1115160B (en, 2012) |
| NL (1) | NL7902832A (en, 2012) |
| PL (1) | PL115524B1 (en, 2012) |
| YU (1) | YU69179A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2855334A1 (de) * | 1978-12-21 | 1980-07-10 | Hoechst Ag | Technetium-99m-markiertes (2,4,5-trimethylacetanilido)-iminodiacetat zur leberfunktionsdiagnostik und verfahren zur herstellung |
| CA1187897A (en) * | 1980-12-29 | 1985-05-28 | Adrian D. Nunn | N-substituted iminodiacetic acids |
| US4574079A (en) * | 1983-05-27 | 1986-03-04 | Gavras Haralambos P | Radiolabeled angiotensin converting enzyme inhibitors for radiolabeling mammalian organ sites |
| US5010191A (en) * | 1985-08-19 | 1991-04-23 | The Regents Of The University Of California | Imaging agents for in vivo magnetic resonance and scintigraphic imaging |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2239617A (en) * | 1939-04-29 | 1941-04-22 | Dow Chemical Co | Preparation of iminodiacetic and aminotriacetic acids |
| US2781391A (en) * | 1956-03-06 | 1957-02-12 | Hans S Mannheimer | Detergent sulphonic acid and sulphate salts of certain amphoteric detergents |
| US2895989A (en) * | 1956-06-22 | 1959-07-21 | Dow Chemical Co | Method for the preparation of iminodiacetic acid |
| US4017956A (en) * | 1973-06-22 | 1977-04-19 | Belknap Donald J | Apparatus for making incandescent lamps and the like |
| US4017596A (en) * | 1975-03-03 | 1977-04-12 | Research Corporation | Radiopharmaceutical chelates and method of external imaging |
| CA1070695A (en) * | 1975-09-02 | 1980-01-29 | Michael D. Loberg | Iminodiacetic acid pharmaceutical |
| CH607920A5 (en, 2012) * | 1976-05-31 | 1978-12-15 | Solco Basel Ag |
-
1978
- 1978-04-10 PL PL1978205961A patent/PL115524B1/pl unknown
-
1979
- 1979-03-22 YU YU00691/79A patent/YU69179A/xx unknown
- 1979-04-02 DE DE19792913173 patent/DE2913173A1/de active Granted
- 1979-04-04 GB GB7911812A patent/GB2018762B/en not_active Expired
- 1979-04-05 FR FR7908625A patent/FR2422397A1/fr active Granted
- 1979-04-06 DD DD79212070A patent/DD142653A5/de not_active IP Right Cessation
- 1979-04-09 IT IT21685/79A patent/IT1115160B/it active
- 1979-04-09 CH CH335879A patent/CH644763A5/de not_active IP Right Cessation
- 1979-04-09 US US06/028,299 patent/US4313926A/en not_active Expired - Lifetime
- 1979-04-09 HU HU79UI280A patent/HU178782B/hu not_active IP Right Cessation
- 1979-04-10 CA CA000325231A patent/CA1161455A/en not_active Expired
- 1979-04-10 BE BE0/194515A patent/BE875466A/xx not_active IP Right Cessation
- 1979-04-10 NL NL7902832A patent/NL7902832A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2913173A1 (de) | 1979-10-11 |
| PL205961A1 (en, 2012) | 1980-04-08 |
| PL115524B1 (en) | 1981-04-30 |
| FR2422397B1 (en, 2012) | 1983-08-05 |
| DE2913173C2 (en, 2012) | 1988-08-11 |
| IT1115160B (it) | 1986-02-03 |
| HU178782B (en) | 1982-06-28 |
| NL7902832A (nl) | 1979-10-12 |
| FR2422397A1 (fr) | 1979-11-09 |
| BE875466A (fr) | 1979-07-31 |
| CH644763A5 (de) | 1984-08-31 |
| US4313926A (en) | 1982-02-02 |
| DD142653A5 (de) | 1980-07-09 |
| GB2018762A (en) | 1979-10-24 |
| GB2018762B (en) | 1982-07-21 |
| YU69179A (en) | 1983-01-21 |
| IT7921685A0 (it) | 1979-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |