JPH05112567A - ６員環を有する巨大環式テトラアザ化合物、その製法及びこれを含有する薬剤 - Google Patents
６員環を有する巨大環式テトラアザ化合物、その製法及びこれを含有する薬剤Info
- Publication number
- JPH05112567A JPH05112567A JP3002602A JP260291A JPH05112567A JP H05112567 A JPH05112567 A JP H05112567A JP 3002602 A JP3002602 A JP 3002602A JP 260291 A JP260291 A JP 260291A JP H05112567 A JPH05112567 A JP H05112567A
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrogen atom
- represent
- general formula
- groups
- 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.)
- Pending
Links
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- 125000000524 functional group Chemical group 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 229920002521 macromolecule Polymers 0.000 claims abstract description 24
- 150000001413 amino acids Chemical class 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 150000002678 macrocyclic compounds Chemical class 0.000 claims abstract description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 18
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 150000001408 amides Chemical class 0.000 claims abstract description 13
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 12
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 12
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 12
- 150000007530 organic bases Chemical class 0.000 claims abstract description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 7
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 99
- 238000000034 method Methods 0.000 claims description 30
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- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
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- -1 hydroxymethylene Chemical group 0.000 abstract description 101
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 6
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
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- 239000000243 solution Substances 0.000 description 55
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 238000004458 analytical method Methods 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 150000002500 ions Chemical class 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000843 powder Substances 0.000 description 19
- 238000001704 evaporation Methods 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000007983 Tris buffer Substances 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 206010028980 Neoplasm Diseases 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002872 contrast media Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000000427 antigen Substances 0.000 description 8
- 230000027455 binding Effects 0.000 description 8
- 229940075613 gadolinium oxide Drugs 0.000 description 8
- 229910001938 gadolinium oxide Inorganic materials 0.000 description 8
- CMIHHWBVHJVIGI-UHFFFAOYSA-N gadolinium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Gd+3].[Gd+3] CMIHHWBVHJVIGI-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 102000036639 antigens Human genes 0.000 description 7
- 108091007433 antigens Proteins 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 210000000056 organ Anatomy 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 5
- 229910052688 Gadolinium Inorganic materials 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000012937 correction Methods 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 230000035699 permeability Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
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- WXIWQHOCXBAFDI-UHFFFAOYSA-N 2,6-bis(methylsulfonylmethyl)pyridine Chemical compound CS(=O)(=O)CC1=CC=CC(CS(C)(=O)=O)=N1 WXIWQHOCXBAFDI-UHFFFAOYSA-N 0.000 description 2
- QEYBMJSQGBIRHS-UHFFFAOYSA-N 2-chloro-3-phenylmethoxypropanoic acid Chemical compound OC(=O)C(Cl)COCC1=CC=CC=C1 QEYBMJSQGBIRHS-UHFFFAOYSA-N 0.000 description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
-
- 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
- A61K51/0482—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 chelates from cyclic ligands, e.g. DOTA
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4001655.2 | 1990-01-18 | ||
| DE4001655A DE4001655A1 (de) | 1990-01-18 | 1990-01-18 | 6-ring enthaltende makrocyclische tetraaza-verbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05112567A true JPH05112567A (ja) | 1993-05-07 |
Family
ID=6398485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3002602A Pending JPH05112567A (ja) | 1990-01-18 | 1991-01-14 | ６員環を有する巨大環式テトラアザ化合物、その製法及びこれを含有する薬剤 |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0438206B1 (zh-CN) |
| JP (1) | JPH05112567A (zh-CN) |
| KR (1) | KR910014377A (zh-CN) |
| AT (1) | ATE141602T1 (zh-CN) |
| AU (1) | AU6981291A (zh-CN) |
| CA (1) | CA2034242A1 (zh-CN) |
| DE (2) | DE4001655A1 (zh-CN) |
| DK (1) | DK0438206T3 (zh-CN) |
| ES (1) | ES2091865T3 (zh-CN) |
| FI (1) | FI94758C (zh-CN) |
| GR (1) | GR3020973T3 (zh-CN) |
| HU (1) | HUT56569A (zh-CN) |
| IE (1) | IE75898B1 (zh-CN) |
| IL (1) | IL96840A0 (zh-CN) |
| NO (1) | NO910191L (zh-CN) |
| NZ (1) | NZ236803A (zh-CN) |
| PT (1) | PT96505B (zh-CN) |
| TW (1) | TW233298B (zh-CN) |
| ZA (1) | ZA91389B (zh-CN) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1121279A (ja) * | 1997-04-18 | 1999-01-26 | Bracco Spa | 低毒性の常磁性金属のキレート錯体 |
| JP2003501430A (ja) * | 1999-06-09 | 2003-01-14 | ゲルベ | ２環式ポリアミノ酸金属複合体、その製法および医療用画像化での使用 |
| JP2009529501A (ja) * | 2006-03-10 | 2009-08-20 | エムディーエス・（カナダ・）インコーポレイテッド | 二官能性ポリアザ大環状キレート剤 |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2644785B1 (fr) * | 1989-03-24 | 1991-07-05 | Guerbet Sa | Nouveaux ligands macrocycliques azotes, procede de preparation, complexes metalliques formes par ces ligands et composition de diagnostic les contenant |
| US5739294A (en) * | 1991-12-10 | 1998-04-14 | The Dow Chemical Company | Bicyclopol yazamacrocyclophosphonic acid complexes for use as contrast agents |
| AU3415493A (en) * | 1991-12-10 | 1993-07-19 | Dow Chemical Company, The | Bicycle-polyazamacrocyclocarboxylic acid complexes, conjugates, preparation and use as contrast agents |
| WO1994026313A1 (en) * | 1993-05-06 | 1994-11-24 | The Dow Chemical Company | Bicyclopolyazamacrocyclocarboxylic acid complexes, their conjugates, processes for their preparation, and use as contrast agents |
| ATE160943T1 (de) * | 1991-12-10 | 1997-12-15 | Dow Chemical Co | Bicycloazamakrocyclophosphon-säure, komplexe, konjugate, kontrastmittel und herstellung |
| ZA929578B (en) * | 1991-12-10 | 1994-06-10 | Dow Chemical Co | Bicyclopolyazamacrocyclocarboxylic acid complexes their conjugates processes for their preparation and use as radiopharmaceuticals |
| US5480990A (en) * | 1991-12-10 | 1996-01-02 | The Dow Chemical Company | Bicyclopolyazamacrocyclocarboxylic acid complexes for use as contrast agents |
| US5428139A (en) * | 1991-12-10 | 1995-06-27 | The Dow Chemical Company | Bicyclopolyazamacrocyclophosphonic acid complexes for use as radiopharmaceuticals |
| AU4237493A (en) * | 1993-05-06 | 1994-12-12 | Dow Chemical Company, The | Bicyclopolyazamacrocyclocarboxylic acid complexes, their conjugates, processes for their preparation, and use as radiopharmaceuticals |
| US5358704A (en) * | 1993-09-30 | 1994-10-25 | Bristol-Myers Squibb | Hepatobiliary tetraazamacrocyclic magnetic resonance contrast agents |
| US5417959A (en) * | 1993-10-04 | 1995-05-23 | Mallinckrodt Medical, Inc. | Functionalized aza-crytand ligands for diagnostic imaging applications |
| SK22795A3 (en) * | 1994-02-21 | 1995-09-13 | Pliva Pharm & Chem Works | Sulfonamidodioxepanes, method of their preparation, intermediates, salts and their using |
| WO1996030377A1 (en) | 1995-03-27 | 1996-10-03 | Isis Pharmaceuticals, Inc. | Nitrogenous macrocyclic compounds |
| US6207826B1 (en) | 1995-03-27 | 2001-03-27 | Isis Pharmaceuticals, Inc. | Macrocyclic compounds having nitrogen-containing linkages |
| KR20000010533A (ko) * | 1996-04-19 | 2000-02-15 | 텍사스 테크 유니버시티 | 시각적 조직 특이성 조영제로서의 형광 킬레이트 |
| EP0977598A1 (en) * | 1997-04-22 | 2000-02-09 | Nycomed Imaging As | Nmr image compounds |
| US8986650B2 (en) | 2005-10-07 | 2015-03-24 | Guerbet | Complex folate-NOTA-Ga68 |
| FR2891830B1 (fr) * | 2005-10-07 | 2011-06-24 | Guerbet Sa | Composes a chaines aminoalcools courtes et complexes metalliques pour l'imagerie medicale |
| EP1940841B9 (fr) | 2005-10-07 | 2017-04-19 | Guerbet | Composes comprenant une partie de reconnaissance d'une cible biologique, couplee a une partie de signal capable de complexer le gallium |
| ES2626582T5 (es) | 2013-04-26 | 2022-10-07 | Guerbet Sa | Formulación de producto de contraste y su procedimiento de preparación asociado |
| US10975060B2 (en) | 2016-11-28 | 2021-04-13 | Bayer Pharma Aktiengesellschaft | High relaxivity gadolinium chelate compounds for use in magnetic resonance imaging |
| PE20211471A1 (es) | 2018-11-23 | 2021-08-05 | Bayer Ag | Formulacion de medios de contraste y proceso para prepararlos |
| FR3091872B1 (fr) | 2019-01-17 | 2020-12-25 | Guerbet Sa | Complexe de gadolinium et d’un ligand chelateur derive de pcta diastereoisomeriquement enrichi et procede de synthese |
| FR3091873B1 (fr) | 2019-01-17 | 2020-12-25 | Guerbet Sa | Complexe de gadolinium et d’un ligand chelateur derive de pcta diastereoisomeriquement enrichi et procede de preparation et de purification |
| WO2022013454A1 (fr) | 2020-07-17 | 2022-01-20 | Guerbet | Procede de preparation d'un ligand chelateur derive de pcta |
| CN114105983B (zh) * | 2021-11-09 | 2023-08-11 | 国科温州研究院(温州生物材料与工程研究所) | 手性1,4,7,10-四氮杂-2,6-吡啶环蕃衍生物及其金属螯合物的制备和应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036945A (en) | 1976-05-03 | 1977-07-19 | The Massachusetts General Hospital | Composition and method for determining the size and location of myocardial infarcts |
| US4331647A (en) | 1980-03-03 | 1982-05-25 | Goldenberg Milton David | Tumor localization and therapy with labeled antibody fragments specific to tumor-associated markers |
| DE3129906C3 (de) * | 1981-07-24 | 1996-12-19 | Schering Ag | Paramagnetische Komplexsalze, deren Herstellung und Mittel zur Verwendung bei der NMR-Diagnostik |
| DE3150917A1 (de) | 1981-12-18 | 1983-06-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | "2-amino-1-(1,3-dioxolan-4-yl)-ethanol-verbindungen, deren herstellung und verwendung zur weiterverarbeitung" |
| NL194579C (nl) * | 1983-01-21 | 2002-08-05 | Schering Ag | Diagnostisch middel. |
| DE3324235A1 (de) * | 1983-07-01 | 1985-01-10 | Schering AG, 1000 Berlin und 4709 Bergkamen | Neue komplexbildner, komplexe und komplexsalze |
| DE3417413A1 (de) | 1984-05-11 | 1985-11-14 | Dr. Karl Thomae Gmbh, 7950 Biberach | Dicarbonsaeure-monohydrazid-derivate, ihre herstellung und ihre verwendung als kopplungskomponenten |
| SE8502573D0 (sv) * | 1985-05-23 | 1985-05-23 | Jouko Kanakre | Fluorescent lanthanide chelates useful as labels of physiologically active materials |
| EP0232751B1 (en) | 1986-01-23 | 1991-09-11 | E.R. Squibb & Sons, Inc. | 1-substituted-4,7,10-triscarboxymethyl-1,4,7,10-tetraazacyclododecane and analogs |
| DE3625417C2 (de) * | 1986-07-28 | 1998-10-08 | Schering Ag | Tetraazacyclododecan-Derivate |
| IT1224416B (it) | 1987-12-24 | 1990-10-04 | Bracco Ind Chimica Spa | Chelanti macrociclici e loro chelati |
| DE3713842A1 (de) | 1987-04-22 | 1988-11-17 | Schering Ag | Substituierte cyclische komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
| DE3869251D1 (de) | 1987-07-16 | 1992-04-23 | Nycomed As | Aminopolycarbonsaeure und ihre derivate. |
| DE3825040A1 (de) * | 1988-07-20 | 1990-01-25 | Schering Ag | 5- oder 6-ring- enthaltende makrocyclische polyaza-verbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| FR2644785B1 (fr) * | 1989-03-24 | 1991-07-05 | Guerbet Sa | Nouveaux ligands macrocycliques azotes, procede de preparation, complexes metalliques formes par ces ligands et composition de diagnostic les contenant |
| DE3938992A1 (de) * | 1989-11-21 | 1991-05-23 | Schering Ag | Kaskadenpolymer-gebundene komplexbildner, deren komplexe und konjugate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
-
1990
- 1990-01-18 DE DE4001655A patent/DE4001655A1/de not_active Withdrawn
- 1990-12-31 IL IL96840A patent/IL96840A0/xx unknown
-
1991
- 1991-01-14 JP JP3002602A patent/JPH05112567A/ja active Pending
- 1991-01-16 AT AT91250008T patent/ATE141602T1/de not_active IP Right Cessation
- 1991-01-16 ES ES91250008T patent/ES2091865T3/es not_active Expired - Lifetime
- 1991-01-16 EP EP91250008A patent/EP0438206B1/de not_active Expired - Lifetime
- 1991-01-16 DK DK91250008.9T patent/DK0438206T3/da active
- 1991-01-16 CA CA002034242A patent/CA2034242A1/en not_active Abandoned
- 1991-01-16 DE DE59108091T patent/DE59108091D1/de not_active Expired - Lifetime
- 1991-01-17 HU HU91156A patent/HUT56569A/hu unknown
- 1991-01-17 NZ NZ236803A patent/NZ236803A/xx unknown
- 1991-01-17 PT PT96505A patent/PT96505B/pt not_active IP Right Cessation
- 1991-01-17 NO NO91910191A patent/NO910191L/no unknown
- 1991-01-18 IE IE16291A patent/IE75898B1/en not_active IP Right Cessation
- 1991-01-18 FI FI910276A patent/FI94758C/fi active
- 1991-01-18 ZA ZA91389A patent/ZA91389B/xx unknown
- 1991-01-18 AU AU69812/91A patent/AU6981291A/en not_active Abandoned
- 1991-01-18 KR KR1019910000816A patent/KR910014377A/ko not_active Application Discontinuation
- 1991-08-06 TW TW080108935A patent/TW233298B/zh active
-
1996
- 1996-09-06 GR GR960402335T patent/GR3020973T3/el unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1121279A (ja) * | 1997-04-18 | 1999-01-26 | Bracco Spa | 低毒性の常磁性金属のキレート錯体 |
| JP2003501430A (ja) * | 1999-06-09 | 2003-01-14 | ゲルベ | ２環式ポリアミノ酸金属複合体、その製法および医療用画像化での使用 |
| JP2009529501A (ja) * | 2006-03-10 | 2009-08-20 | エムディーエス・（カナダ・）インコーポレイテッド | 二官能性ポリアザ大環状キレート剤 |
| US8518715B2 (en) | 2006-03-10 | 2013-08-27 | Nordion (Canada) Inc. | Bifunctional polyazamacrocyclic chelating agents |
Also Published As
| Publication number | Publication date |
|---|---|
| PT96505A (pt) | 1991-10-15 |
| HUT56569A (en) | 1991-09-30 |
| KR910014377A (ko) | 1991-08-31 |
| HU910156D0 (en) | 1991-08-28 |
| EP0438206A1 (de) | 1991-07-24 |
| IL96840A0 (en) | 1991-09-16 |
| DE59108091D1 (de) | 1996-09-26 |
| NO910191L (no) | 1991-07-19 |
| FI94758B (fi) | 1995-07-14 |
| AU6981291A (en) | 1991-08-22 |
| EP0438206B1 (de) | 1996-08-21 |
| GR3020973T3 (en) | 1996-12-31 |
| FI910276A (fi) | 1991-07-19 |
| CA2034242A1 (en) | 1991-07-19 |
| DE4001655A1 (de) | 1991-07-25 |
| FI94758C (fi) | 1995-10-25 |
| IE75898B1 (en) | 1997-09-24 |
| FI910276A0 (fi) | 1991-01-18 |
| DK0438206T3 (zh-CN) | 1997-01-20 |
| ATE141602T1 (de) | 1996-09-15 |
| PT96505B (pt) | 1998-07-31 |
| TW233298B (zh-CN) | 1994-11-01 |
| ES2091865T3 (es) | 1996-11-16 |
| IE910162A1 (en) | 1991-07-31 |
| NZ236803A (en) | 1993-08-26 |
| NO910191D0 (no) | 1991-01-17 |
| ZA91389B (en) | 1991-10-30 |
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