LV10867B - Process for the preparation of azamacrocyclic or acyclic aminophosphonate ester derivatives - Google Patents
Process for the preparation of azamacrocyclic or acyclic aminophosphonate ester derivatives Download PDFInfo
- Publication number
- LV10867B LV10867B LVP-94-99A LV940099A LV10867B LV 10867 B LV10867 B LV 10867B LV 940099 A LV940099 A LV 940099A LV 10867 B LV10867 B LV 10867B
- Authority
- LV
- Latvia
- Prior art keywords
- formula
- thf
- tetrahydrofuran
- triene
- paraformaldehyde
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 104
- 238000002360 preparation method Methods 0.000 title claims description 30
- -1 acyclic aminophosphonate ester Chemical class 0.000 title claims description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 110
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 41
- 229920002866 paraformaldehyde Polymers 0.000 claims description 37
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 26
- 230000007062 hydrolysis Effects 0.000 claims description 24
- 238000006460 hydrolysis reaction Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000003446 ligand Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 16
- 239000007983 Tris buffer Substances 0.000 claims description 14
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052700 potassium Inorganic materials 0.000 claims description 12
- 229910052708 sodium Inorganic materials 0.000 claims description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 9
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- 239000006184 cosolvent Substances 0.000 claims description 8
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 6
- VPGQJHBMALMMJQ-UHFFFAOYSA-N 1-(pyridin-2-ylmethyl)-1,4,7,10-tetrazacyclododecane Chemical compound C=1C=CC=NC=1CN1CCNCCNCCNCC1 VPGQJHBMALMMJQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003916 ethylene diamine group Chemical group 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 7
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 claims 5
- 238000000926 separation method Methods 0.000 claims 4
- 238000002955 isolation Methods 0.000 claims 3
- 238000007363 ring formation reaction Methods 0.000 claims 3
- DEVWEFBXXYMHIL-UHFFFAOYSA-N CCCOP(O)=O Chemical compound CCCOP(O)=O DEVWEFBXXYMHIL-UHFFFAOYSA-N 0.000 claims 2
- WCJLOEFXANROAO-UHFFFAOYSA-N CCCCOP(O)=O Chemical compound CCCCOP(O)=O WCJLOEFXANROAO-UHFFFAOYSA-N 0.000 claims 1
- FJHPGVWPKINBMP-UHFFFAOYSA-H [Ca++].[Ca++].[Ca++].[O-]P([O-])=O.[O-]P([O-])=O.[O-]P([O-])=O Chemical compound [Ca++].[Ca++].[Ca++].[O-]P([O-])=O.[O-]P([O-])=O.[O-]P([O-])=O FJHPGVWPKINBMP-UHFFFAOYSA-H 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 101150054171 thf1 gene Proteins 0.000 claims 1
- 150000005671 trienes Chemical class 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 33
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 18
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 16
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000000243 solution Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000002015 acyclic group Chemical group 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000004679 31P NMR spectroscopy Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229940120146 EDTMP Drugs 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RCXMQNIDOFXYDO-UHFFFAOYSA-N [4,7,10-tris(phosphonomethyl)-1,4,7,10-tetrazacyclododec-1-yl]methylphosphonic acid Chemical compound OP(O)(=O)CN1CCN(CP(O)(O)=O)CCN(CP(O)(O)=O)CCN(CP(O)(O)=O)CC1 RCXMQNIDOFXYDO-UHFFFAOYSA-N 0.000 description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 description 3
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 3
- 150000003009 phosphonic acids Chemical class 0.000 description 3
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 3
- 238000000607 proton-decoupled 31P nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002518 distortionless enhancement with polarization transfer Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000008947 Amm Methods 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000012614 Q-Sepharose Substances 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 229940090960 diethylenetriamine pentamethylene phosphonic acid Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 238000000079 presaturation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/065,963 US5714604A (en) | 1993-05-06 | 1993-05-06 | Process for the preparation of azamacrocyclic or acyclic aminophosphonate ester derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LV10867A LV10867A (lv) | 1995-10-20 |
| LV10867B true LV10867B (en) | 1996-08-20 |
Family
ID=22066341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LVP-94-99A LV10867B (en) | 1993-05-06 | 1994-05-06 | Process for the preparation of azamacrocyclic or acyclic aminophosphonate ester derivatives |
Country Status (34)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6207826B1 (en) | 1995-03-27 | 2001-03-27 | Isis Pharmaceuticals, Inc. | Macrocyclic compounds having nitrogen-containing linkages |
| US6107482A (en) | 1995-03-27 | 2000-08-22 | Isis Pharmaceuticals, Inc. | Nitrogenous macrocyclic compounds |
| WO2000076556A2 (en) * | 1999-06-11 | 2000-12-21 | Neorx Corporation | High dose radionuclide complexes for bone marrow suppression |
| US7094885B2 (en) * | 1999-07-11 | 2006-08-22 | Neorx Corporation | Skeletal-targeted radiation to treat bone-associated pathologies |
| US6794371B1 (en) * | 1999-10-18 | 2004-09-21 | The Dow Chemical Company | Aminoalkylenephosphonates for treatment of bone disorders |
| AU1092601A (en) * | 1999-10-18 | 2001-04-30 | Dow Global Technologies Inc. | Aminoalkylenephosphonates for treatment of bone disorders |
| US6565828B2 (en) * | 2000-04-07 | 2003-05-20 | Bristol-Myers Squibb Company | Macrocyclic chelants for metallopharmaceuticals |
| AU2002249935A1 (en) | 2001-01-08 | 2002-08-19 | Neorx Corporation | Radioactively labelled conjugates of phosphonates |
| ATE309254T1 (de) * | 2001-10-22 | 2005-11-15 | Univ Texas Tech | Gewebespezifische fluoreszierende chelate |
| DE60212424T2 (de) * | 2001-10-22 | 2006-10-12 | Dow Global Technologies, Inc., Midland | Radiopharmazeutisches mittel zur behandlung von krebs im frühstadium |
| JP2005516933A (ja) | 2001-12-13 | 2005-06-09 | ダウ グローバル テクノロジーズ インコーポレイティド | 放射性医薬による骨髄炎の治療 |
| US20050112066A1 (en) * | 2003-11-26 | 2005-05-26 | Concat Lp, A California Limited Partnership | Complexes of cyclic polyaza chelators with cations of alkaline earth metals for enhanced biological activity |
| US20060210479A1 (en) * | 2004-08-10 | 2006-09-21 | Dow Global Technologies Inc. | Targeting chelants and chelates |
| CN112442069A (zh) * | 2019-08-28 | 2021-03-05 | 广东广山新材料股份有限公司 | 一种带有胺基的含磷阻燃剂及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5362476A (en) * | 1984-10-18 | 1994-11-08 | Board Of Regents, The University Of Texas System | Alkyl phosphonate polyazamacrocyclic cheates for MRI |
| GB8817185D0 (en) * | 1988-07-19 | 1988-08-24 | Interox Chemicals Ltd | Organic polyphosphonates |
| GB8903023D0 (en) * | 1989-02-10 | 1989-03-30 | Parker David | Chemical compounds |
| US5342936A (en) * | 1989-02-10 | 1994-08-30 | David Parker | Tetra-aza macrocycles and processes for their preparation |
| ES2091251T3 (es) * | 1989-11-27 | 1996-11-01 | Concat Ltd | Perfeccionamiento de la imagen en la mri del hueso y del tejido emparentado utilizando complejos de cationes paramagneticos y ligandos polifosfonato. |
| US5236695A (en) * | 1989-11-27 | 1993-08-17 | Concat, Ltd. | MRI image enhancement of bone and related tissue using complexes of paramagnetic cations and polyphosphonate ligands |
| US5385893A (en) * | 1993-05-06 | 1995-01-31 | The Dow Chemical Company | Tricyclopolyazamacrocyclophosphonic acids, complexes and derivatives thereof, for use as contrast agents |
| US5606053A (en) * | 1995-05-02 | 1997-02-25 | Johnson Matthey Plc | Process for preparing 1,1'-[1,4-phenylenebis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane |
-
1993
- 1993-05-06 US US08/065,963 patent/US5714604A/en not_active Expired - Lifetime
-
1994
- 1994-05-04 DZ DZ940043A patent/DZ1777A1/fr active
- 1994-05-04 AU AU69086/94A patent/AU682190B2/en not_active Ceased
- 1994-05-04 KR KR1019950704944A patent/KR100311560B1/ko not_active Expired - Fee Related
- 1994-05-04 DE DE69414382T patent/DE69414382T2/de not_active Expired - Lifetime
- 1994-05-04 WO PCT/US1994/005134 patent/WO1994026753A1/en not_active Ceased
- 1994-05-04 JP JP52562094A patent/JP3556669B2/ja not_active Expired - Fee Related
- 1994-05-04 ES ES94917333T patent/ES2123137T3/es not_active Expired - Lifetime
- 1994-05-04 CA CA002162170A patent/CA2162170C/en not_active Expired - Fee Related
- 1994-05-04 HU HU9503175A patent/HU223769B1/hu not_active IP Right Cessation
- 1994-05-04 EP EP94917333A patent/EP0698029B1/en not_active Expired - Lifetime
- 1994-05-04 AT AT94917333T patent/ATE172978T1/de not_active IP Right Cessation
- 1994-05-04 CN CN94192530A patent/CN1042537C/zh not_active Expired - Fee Related
- 1994-05-04 DK DK94917333T patent/DK0698029T3/da active
- 1994-05-04 PL PL94311651A patent/PL180756B1/pl not_active IP Right Cessation
- 1994-05-04 UA UA95114920A patent/UA44704C2/uk unknown
- 1994-05-04 RO RO95-01927A patent/RO115883B1/ro unknown
- 1994-05-04 CZ CZ19952890A patent/CZ290993B6/cs not_active IP Right Cessation
- 1994-05-05 RU RU95122389A patent/RU2135507C1/ru not_active IP Right Cessation
- 1994-05-05 MA MA23494A patent/MA23186A1/fr unknown
- 1994-05-05 IS IS4158A patent/IS1735B/is unknown
- 1994-05-05 IL IL10956194A patent/IL109561A/en not_active IP Right Cessation
- 1994-05-06 TN TNTNSN94040A patent/TNSN94040A1/fr unknown
- 1994-05-06 ZA ZA943158A patent/ZA943158B/xx unknown
- 1994-05-06 CO CO94018967A patent/CO4230080A1/es unknown
- 1994-05-06 LV LVP-94-99A patent/LV10867B/en unknown
- 1994-05-06 LT LTIP1925A patent/LT3713B/lt not_active IP Right Cessation
- 1994-05-06 AP APAP/P/1994/000639A patent/AP543A/en active
- 1994-05-07 EG EG26094A patent/EG20296A/xx active
- 1994-05-18 TW TW083104130A patent/TW273549B/zh not_active IP Right Cessation
- 1994-07-14 EE EE9400087A patent/EE03159B1/xx not_active IP Right Cessation
-
1995
- 1995-11-03 FI FI955281A patent/FI115632B/fi not_active IP Right Cessation
- 1995-11-06 NO NO953800A patent/NO304742B1/no not_active IP Right Cessation
- 1995-12-05 BG BG100193A patent/BG62775B1/bg unknown
Also Published As
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