ZA200202742B - Calcium complex of phosphorus containing ethylenediamine derivatives. - Google Patents
Calcium complex of phosphorus containing ethylenediamine derivatives. Download PDFInfo
- Publication number
- ZA200202742B ZA200202742B ZA200202742A ZA200202742A ZA200202742B ZA 200202742 B ZA200202742 B ZA 200202742B ZA 200202742 A ZA200202742 A ZA 200202742A ZA 200202742 A ZA200202742 A ZA 200202742A ZA 200202742 B ZA200202742 B ZA 200202742B
- Authority
- ZA
- South Africa
- Prior art keywords
- kappa
- carboxy
- bis
- calcium
- mmol
- Prior art date
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- 239000011575 calcium Substances 0.000 title claims description 53
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims description 24
- 229910052791 calcium Inorganic materials 0.000 title claims description 24
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 title description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 2
- 239000011574 phosphorus Substances 0.000 title description 2
- 229910052698 phosphorus Inorganic materials 0.000 title description 2
- -1 carboxy- Chemical class 0.000 claims description 110
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 43
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 39
- 238000004519 manufacturing process Methods 0.000 claims description 38
- 239000000872 buffer Substances 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 238000009472 formulation Methods 0.000 claims description 33
- 239000000243 solution Substances 0.000 claims description 29
- 229960003194 meglumine Drugs 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 25
- 229940075613 gadolinium oxide Drugs 0.000 claims description 23
- 229910001938 gadolinium oxide Inorganic materials 0.000 claims description 23
- CMIHHWBVHJVIGI-UHFFFAOYSA-N gadolinium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Gd+3].[Gd+3] CMIHHWBVHJVIGI-UHFFFAOYSA-N 0.000 claims description 23
- 239000011734 sodium Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000008177 pharmaceutical agent Substances 0.000 claims description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 238000003745 diagnosis Methods 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 229910001385 heavy metal Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 3
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 3
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 238000003384 imaging method Methods 0.000 claims description 3
- 229960003104 ornithine Drugs 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 2
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims 2
- CUGDYSSBTWBKII-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO CUGDYSSBTWBKII-LXGUWJNJSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims 1
- 229910001948 sodium oxide Inorganic materials 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- ZSDLYSDDELEVDD-UFTMZEDQSA-K 2-[[(2r)-2-[bis(carboxylatomethyl)amino]-3-[(4,4-diphenylcyclohexyl)oxy-oxidophosphoryl]oxypropyl]-[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate;gadolinium(3+);hydron Chemical compound [H+].[H+].[H+].[Gd+3].C1CC(OP([O-])(=O)OC[C@@H](CN(CCN(CC([O-])=O)CC([O-])=O)CC(=O)[O-])N(CC([O-])=O)CC([O-])=O)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 ZSDLYSDDELEVDD-UFTMZEDQSA-K 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000000706 filtrate Substances 0.000 description 26
- 239000008139 complexing agent Substances 0.000 description 24
- 229910052688 Gadolinium Inorganic materials 0.000 description 21
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 21
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 18
- 239000008367 deionised water Substances 0.000 description 18
- 229910021641 deionized water Inorganic materials 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 16
- 239000003446 ligand Substances 0.000 description 16
- 239000000843 powder Substances 0.000 description 13
- 238000004108 freeze drying Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 229910000019 calcium carbonate Inorganic materials 0.000 description 9
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- 239000000920 calcium hydroxide Substances 0.000 description 8
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002872 contrast media Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 102000008100 Human Serum Albumin Human genes 0.000 description 2
- 108091006905 Human Serum Albumin Proteins 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 206010027439 Metal poisoning Diseases 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- LGMLJQFQKXPRGA-VPVMAENOSA-K gadopentetate dimeglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O LGMLJQFQKXPRGA-VPVMAENOSA-K 0.000 description 2
- 208000010501 heavy metal poisoning Diseases 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 229960003330 pentetic acid Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000002059 diagnostic imaging Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000003331 infrared imaging Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000012285 ultrasound imaging Methods 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/117—Esters of phosphoric acids with cycloaliphatic alcohols
-
- 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
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
- A61K49/103—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being acyclic, e.g. DTPA
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/04—Chelating agents
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Radiology & Medical Imaging (AREA)
- Epidemiology (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Cosmetics (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Absorbent Articles And Supports Therefor (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1999144893 DE19944893C2 (de) | 1999-09-09 | 1999-09-09 | Calcium-Komplex von [[(4R)-4-[bis[(carboxy-.kappa.O)methyl]amino-. kappa.N]-6,9-bis[(carboxy-.kappa.O)methyl]-1-[(4,4-diphenylcyclohexyl)oxy]-1-hydroxy-2-oxa-6,9-diaza-1-phosphaundecan-11-yl-säure-.kappa.N6, .kappa.N9,.kappa.O11]1-oxidato(6-)]-, hexahydrogen, dessen Salze und diese Komplexe enthaltende pharmazeutische Mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200202742B true ZA200202742B (en) | 2003-09-23 |
Family
ID=7922563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200202742A ZA200202742B (en) | 1999-09-09 | 2002-04-08 | Calcium complex of phosphorus containing ethylenediamine derivatives. |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1210353B1 (ja) |
| JP (1) | JP2003508537A (ja) |
| KR (1) | KR100650090B1 (ja) |
| CN (1) | CN100341883C (ja) |
| AT (1) | ATE245159T1 (ja) |
| AU (1) | AU783982B2 (ja) |
| BG (1) | BG65280B1 (ja) |
| BR (1) | BR0013871A (ja) |
| CA (1) | CA2380766C (ja) |
| CZ (1) | CZ2002834A3 (ja) |
| DE (2) | DE19964224B4 (ja) |
| DK (1) | DK1210353T3 (ja) |
| EE (1) | EE05106B1 (ja) |
| ES (1) | ES2202178T3 (ja) |
| HK (1) | HK1050202A1 (ja) |
| HR (1) | HRP20020302B1 (ja) |
| HU (1) | HUP0202873A3 (ja) |
| IL (1) | IL148563A (ja) |
| MX (1) | MXPA02001583A (ja) |
| NO (1) | NO20021167D0 (ja) |
| NZ (1) | NZ517708A (ja) |
| PL (1) | PL354749A1 (ja) |
| PT (1) | PT1210353E (ja) |
| RS (1) | RS50125B (ja) |
| RU (1) | RU2247727C2 (ja) |
| SK (1) | SK3242002A3 (ja) |
| TW (1) | TWI263641B (ja) |
| UA (1) | UA74165C2 (ja) |
| WO (1) | WO2001018011A1 (ja) |
| ZA (1) | ZA200202742B (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201514188A (zh) | 2013-03-13 | 2015-04-16 | Lantheus Medical Imaging Inc | 製備釓磷維塞三鈉單水合物之方法 |
| EP4077271A1 (en) | 2019-12-20 | 2022-10-26 | Bracco Imaging SPA | Calcium bopta complex |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3129906C3 (de) * | 1981-07-24 | 1996-12-19 | Schering Ag | Paramagnetische Komplexsalze, deren Herstellung und Mittel zur Verwendung bei der NMR-Diagnostik |
| TW319763B (ja) * | 1995-02-01 | 1997-11-11 | Epix Medical Inc | |
| US5919967A (en) * | 1997-04-11 | 1999-07-06 | Epix Medical, Inc. | Process for synthesizing phosphodiesters |
-
1999
- 1999-09-09 DE DE19964224A patent/DE19964224B4/de not_active Expired - Fee Related
-
2000
- 2000-06-09 UA UA2002042826A patent/UA74165C2/uk unknown
- 2000-09-06 EP EP00967650A patent/EP1210353B1/en not_active Revoked
- 2000-09-06 IL IL14856300A patent/IL148563A/en not_active IP Right Cessation
- 2000-09-06 PL PL00354749A patent/PL354749A1/xx unknown
- 2000-09-06 HU HU0202873A patent/HUP0202873A3/hu unknown
- 2000-09-06 WO PCT/EP2000/008694 patent/WO2001018011A1/en active IP Right Grant
- 2000-09-06 KR KR1020027003005A patent/KR100650090B1/ko not_active IP Right Cessation
- 2000-09-06 CN CNB008126879A patent/CN100341883C/zh not_active Expired - Fee Related
- 2000-09-06 DK DK00967650T patent/DK1210353T3/da active
- 2000-09-06 MX MXPA02001583A patent/MXPA02001583A/es active IP Right Grant
- 2000-09-06 CA CA002380766A patent/CA2380766C/en not_active Expired - Fee Related
- 2000-09-06 PT PT00967650T patent/PT1210353E/pt unknown
- 2000-09-06 RU RU2002107456/04A patent/RU2247727C2/ru not_active IP Right Cessation
- 2000-09-06 CZ CZ2002834A patent/CZ2002834A3/cs unknown
- 2000-09-06 BR BR0013871-1A patent/BR0013871A/pt not_active Application Discontinuation
- 2000-09-06 AT AT00967650T patent/ATE245159T1/de not_active IP Right Cessation
- 2000-09-06 JP JP2001522234A patent/JP2003508537A/ja active Pending
- 2000-09-06 RS YUP-161/02A patent/RS50125B/sr unknown
- 2000-09-06 SK SK324-2002A patent/SK3242002A3/sk not_active Application Discontinuation
- 2000-09-06 AU AU77749/00A patent/AU783982B2/en not_active Ceased
- 2000-09-06 ES ES00967650T patent/ES2202178T3/es not_active Expired - Lifetime
- 2000-09-06 DE DE60003931T patent/DE60003931T2/de not_active Revoked
- 2000-09-06 NZ NZ517708A patent/NZ517708A/en unknown
- 2000-09-06 EE EEP200200090A patent/EE05106B1/xx not_active IP Right Cessation
- 2000-09-28 TW TW089118643A patent/TWI263641B/zh active
-
2002
- 2002-03-07 BG BG106488A patent/BG65280B1/bg unknown
- 2002-03-08 NO NO20021167A patent/NO20021167D0/no not_active Application Discontinuation
- 2002-04-08 ZA ZA200202742A patent/ZA200202742B/en unknown
- 2002-04-09 HR HR20020302A patent/HRP20020302B1/xx not_active IP Right Cessation
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2003
- 2003-04-08 HK HK03102469A patent/HK1050202A1/xx not_active IP Right Cessation
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