DE4028139A1 - Verwendung der komplexe radioaktiver metallionen mit all-cis-1,3,5-triamino-2,4,6-cyclohexantriol und seinen derivaten fuer roentgendiagnostische zwecke und in der tumortherapie sowie zur herstellung von mitteln fuer roentgendiagnostische zwecke und fuer die tumortherapie - Google Patents
Verwendung der komplexe radioaktiver metallionen mit all-cis-1,3,5-triamino-2,4,6-cyclohexantriol und seinen derivaten fuer roentgendiagnostische zwecke und in der tumortherapie sowie zur herstellung von mitteln fuer roentgendiagnostische zwecke und fuer die tumortherapieInfo
- Publication number
- DE4028139A1 DE4028139A1 DE4028139A DE4028139A DE4028139A1 DE 4028139 A1 DE4028139 A1 DE 4028139A1 DE 4028139 A DE4028139 A DE 4028139A DE 4028139 A DE4028139 A DE 4028139A DE 4028139 A1 DE4028139 A1 DE 4028139A1
- Authority
- DE
- Germany
- Prior art keywords
- use according
- alkyl groups
- groups
- future
- alkyl
- 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.)
- Withdrawn
Links
- 230000002285 radioactive effect Effects 0.000 title claims abstract description 26
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 16
- 238000002560 therapeutic procedure Methods 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000003446 ligand Substances 0.000 claims description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052772 Samarium Inorganic materials 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 229910052713 technetium Inorganic materials 0.000 claims description 2
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 229910052702 rhenium Inorganic materials 0.000 claims 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 description 17
- 239000002184 metal Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 150000001768 cations Chemical class 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- -1 1,3,5-triamino-2,4,5-triamino-2,4,6-trihydroxycyclohexane Chemical compound 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- OKPBGFSFTUQDJP-UHFFFAOYSA-N 2,4,6-triaminocyclohexane-1,3,5-triol Chemical compound NC1C(O)C(N)C(O)C(N)C1O OKPBGFSFTUQDJP-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 229910018828 PO3H2 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- JYLCAUPFUURAML-UHFFFAOYSA-H [Tc](Cl)(Cl)(Cl)(Cl)(Cl)Cl Chemical compound [Tc](Cl)(Cl)(Cl)(Cl)(Cl)Cl JYLCAUPFUURAML-UHFFFAOYSA-H 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- FNTHQRXVZDCWSP-UHFFFAOYSA-N cyclohexane-1,1,2-triol Chemical compound OC1CCCCC1(O)O FNTHQRXVZDCWSP-UHFFFAOYSA-N 0.000 description 1
- 238000002059 diagnostic imaging Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- PRVOBRCYHYXCMU-UHFFFAOYSA-H hexafluorotechnetium Chemical compound F[Tc](F)(F)(F)(F)F PRVOBRCYHYXCMU-UHFFFAOYSA-H 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003495 technetium Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000003325 tomography Methods 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4028139A DE4028139A1 (de) | 1990-09-05 | 1990-09-05 | Verwendung der komplexe radioaktiver metallionen mit all-cis-1,3,5-triamino-2,4,6-cyclohexantriol und seinen derivaten fuer roentgendiagnostische zwecke und in der tumortherapie sowie zur herstellung von mitteln fuer roentgendiagnostische zwecke und fuer die tumortherapie |
| KR1019920701057A KR920702235A (ko) | 1990-09-05 | 1991-09-05 | 모든-시스-1,3,5-트리아미노-2,4,6-시클로헥산트리올 및 그 유도체와 방사능 금속이온의 착물에 대한 방사능 진단 목적과 종양치료를 위한 용도 및 방사능 진단 목적용과 종양치료용 시약의 제조를 위한 용도 |
| PT98869A PT98869A (pt) | 1990-09-05 | 1991-09-05 | Processo para a preparacao de complexos de ioes radioactivos e de all-cis-1,3,5-triamino-2,4,6-ciclo-hexanotriol ou dos seus derivados e de composicoes farmaceuticas para o diagnostico radiografico e a terapia de tumores que os contem |
| JP3514779A JPH05502456A (ja) | 1990-09-05 | 1991-09-05 | 放射線診断用および腫瘍治療のための並びに放射線診断用剤および腫瘍治療剤の製造のための放射性金属イオンと全―シス―１，３，５―トリアミノ―２，４，６―シクロヘキサントリオールおよびその誘導体との錯体の使用 |
| EP91915523A EP0504339A1 (de) | 1990-09-05 | 1991-09-05 | VERWENDUNG DER KOMPLEXE RADIOAKTIVER METALLIONEN MIT all-cis-1,3,5-TRIAMINO-2,4,6-CYCLOHEXANTRIOL UND SEINEN DERIVATEN FÜR RÖNTGENDIAGNOSTISCHE ZWECKE UND IN DER TUMORTHERAPIE SOWIE ZUR HERSTELLUNG VON MITTELN FÜR RÖNTGENDIAGNOSTISCHE ZWECKE UND FÜR DIE TUMORTHERAPIE |
| PCT/EP1991/001679 WO1992004056A1 (de) | 1990-09-05 | 1991-09-05 | VERWENDUNG DER KOMPLEXE RADIOAKTIVER METALLIONEN MIT all-cis-1,3,5-TRIAMINO-2,4,6-CYCLOHEXANTRIOL UND SEINEN DERIVATEN FÜR RÖNTGENDIAGNOSTISCHE ZWECKE UND IN DER TUMORTHERAPIE SOWIE ZUR HERSTELLUNG VON MITTELN FÜR RÖNTGENDIAGNOSTISCHE ZWECKE UND FÜR DIE TUMORTHERAPIE |
| AU84367/91A AU658148B2 (en) | 1990-09-05 | 1991-09-05 | Use of radioactive metal ion complexes with all-cis-1,3,5-triamino-2,4,6-cyclohexantriol and their derivates for x-ray diagnosis and in tumor therapy as well asfor producing x-ray diagnostic and tumor therapy agents |
| MX9100967A MX9100967A (es) | 1990-09-05 | 1991-09-05 | Uso del complejo de iones metalicos radioactivos con allcis-1,3,5-triamino-2,4,5-ciclohexanotriol y sus derivados para propositos de diagnosticos por rayos x y en la terapia de tumores asi como en la preparacion de medios para propositos de |
| CA002073050A CA2073050A1 (en) | 1990-09-05 | 1991-09-05 | Use of complexes of radioactive metal ions with all-cis-1,3,5-triamino-2,4, 6-cyclohexanetriol and its derivatives for radiodiagnostic purposes and in tumor therapy and for the preparation of agents for radiodiagnost c purposes and for tumor therapy |
| TW080109680A TW197951B (enExample) | 1990-09-05 | 1991-12-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4028139A DE4028139A1 (de) | 1990-09-05 | 1990-09-05 | Verwendung der komplexe radioaktiver metallionen mit all-cis-1,3,5-triamino-2,4,6-cyclohexantriol und seinen derivaten fuer roentgendiagnostische zwecke und in der tumortherapie sowie zur herstellung von mitteln fuer roentgendiagnostische zwecke und fuer die tumortherapie |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4028139A1 true DE4028139A1 (de) | 1992-03-12 |
Family
ID=6413642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4028139A Withdrawn DE4028139A1 (de) | 1990-09-05 | 1990-09-05 | Verwendung der komplexe radioaktiver metallionen mit all-cis-1,3,5-triamino-2,4,6-cyclohexantriol und seinen derivaten fuer roentgendiagnostische zwecke und in der tumortherapie sowie zur herstellung von mitteln fuer roentgendiagnostische zwecke und fuer die tumortherapie |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0504339A1 (enExample) |
| JP (1) | JPH05502456A (enExample) |
| KR (1) | KR920702235A (enExample) |
| AU (1) | AU658148B2 (enExample) |
| CA (1) | CA2073050A1 (enExample) |
| DE (1) | DE4028139A1 (enExample) |
| MX (1) | MX9100967A (enExample) |
| PT (1) | PT98869A (enExample) |
| TW (1) | TW197951B (enExample) |
| WO (1) | WO1992004056A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6056938A (en) | 1995-02-21 | 2000-05-02 | Imarx Pharaceutical Corp. | Cationic lipids and the use thereof |
| WO2013171048A1 (en) | 2012-05-18 | 2013-11-21 | Bayer Pharma Aktiengesellschaft | Bis azainositol heavy metal complexes for x-ray imaging |
| EP2796152A1 (en) | 2013-04-25 | 2014-10-29 | Bayer Pharma Aktiengesellschaft | Unsymmetrical Bis Azainositol Hafnium Complexes for X-Ray Imaging |
| EP2873670A1 (en) | 2013-11-14 | 2015-05-20 | Bayer Pharma Aktiengesellschaft | Bis azainositol zirconium complexes for X-ray imaging |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3503614A1 (de) * | 1985-02-02 | 1986-08-07 | Laboratorien Hausmann AG, St. Gallen | All-cis-1,3,5-triamino-2,4,6-cyclohexantriol-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate |
| GB8900719D0 (en) * | 1989-01-13 | 1989-03-08 | Nycomed As | Compounds |
| CH679742A5 (enExample) * | 1990-01-09 | 1992-04-15 | Byk Gulden Lomberg Chem Fab |
-
1990
- 1990-09-05 DE DE4028139A patent/DE4028139A1/de not_active Withdrawn
-
1991
- 1991-09-05 PT PT98869A patent/PT98869A/pt not_active Application Discontinuation
- 1991-09-05 WO PCT/EP1991/001679 patent/WO1992004056A1/de not_active Ceased
- 1991-09-05 KR KR1019920701057A patent/KR920702235A/ko not_active Ceased
- 1991-09-05 CA CA002073050A patent/CA2073050A1/en not_active Abandoned
- 1991-09-05 MX MX9100967A patent/MX9100967A/es unknown
- 1991-09-05 EP EP91915523A patent/EP0504339A1/de not_active Withdrawn
- 1991-09-05 AU AU84367/91A patent/AU658148B2/en not_active Ceased
- 1991-09-05 JP JP3514779A patent/JPH05502456A/ja active Pending
- 1991-12-10 TW TW080109680A patent/TW197951B/zh active
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6056938A (en) | 1995-02-21 | 2000-05-02 | Imarx Pharaceutical Corp. | Cationic lipids and the use thereof |
| WO2013171048A1 (en) | 2012-05-18 | 2013-11-21 | Bayer Pharma Aktiengesellschaft | Bis azainositol heavy metal complexes for x-ray imaging |
| EP2796152A1 (en) | 2013-04-25 | 2014-10-29 | Bayer Pharma Aktiengesellschaft | Unsymmetrical Bis Azainositol Hafnium Complexes for X-Ray Imaging |
| WO2014173857A1 (en) | 2013-04-25 | 2014-10-30 | Bayer Pharma Aktiengesellschaft | Bis azainositol hafnium complexes for x-ray imaging |
| EP2873670A1 (en) | 2013-11-14 | 2015-05-20 | Bayer Pharma Aktiengesellschaft | Bis azainositol zirconium complexes for X-ray imaging |
| WO2015071201A1 (en) | 2013-11-14 | 2015-05-21 | Bayer Pharma Aktiengesellschaft | Bis azainositol zirconium complexes for x-ray imaging |
Also Published As
| Publication number | Publication date |
|---|---|
| AU8436791A (en) | 1992-03-30 |
| WO1992004056A1 (de) | 1992-03-19 |
| JPH05502456A (ja) | 1993-04-28 |
| CA2073050A1 (en) | 1992-03-06 |
| KR920702235A (ko) | 1992-09-03 |
| EP0504339A1 (de) | 1992-09-23 |
| MX9100967A (es) | 1992-05-04 |
| PT98869A (pt) | 1992-07-31 |
| TW197951B (enExample) | 1993-01-11 |
| AU658148B2 (en) | 1995-04-06 |
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