BG62775B1 - Метод за получаване на азамакроциклични или ациклични аминофосфонатни естерни производни - Google Patents
Метод за получаване на азамакроциклични или ациклични аминофосфонатни естерни производни Download PDFInfo
- Publication number
- BG62775B1 BG62775B1 BG100193A BG10019395A BG62775B1 BG 62775 B1 BG62775 B1 BG 62775B1 BG 100193 A BG100193 A BG 100193A BG 10019395 A BG10019395 A BG 10019395A BG 62775 B1 BG62775 B1 BG 62775B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- pentadeca
- paraformaldehyde
- alkyl
- tetraazabicyclo
- triene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 62
- -1 acyclic aminophosphonate ester Chemical class 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims description 27
- 229930040373 Paraformaldehyde Natural products 0.000 claims abstract description 20
- 229920002866 paraformaldehyde Polymers 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
- 239000003446 ligand Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 claims description 14
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 13
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 claims description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 9
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 9
- 239000007983 Tris buffer Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 6
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 claims description 6
- 229940120146 EDTMP Drugs 0.000 claims description 5
- 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 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000006184 cosolvent Substances 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 3
- WCJLOEFXANROAO-UHFFFAOYSA-N CCCCOP(O)=O Chemical compound CCCCOP(O)=O WCJLOEFXANROAO-UHFFFAOYSA-N 0.000 claims description 2
- DEVWEFBXXYMHIL-UHFFFAOYSA-N CCCOP(O)=O Chemical compound CCCOP(O)=O DEVWEFBXXYMHIL-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001923 cyclic compounds Chemical class 0.000 claims description 2
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000003007 phosphonic acid derivatives Chemical class 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- LNMUPMQUMCDOKO-UHFFFAOYSA-N 3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-triene Chemical compound C1NCCNCCNCC2=CC=CC1=N2 LNMUPMQUMCDOKO-UHFFFAOYSA-N 0.000 claims 5
- 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 3
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- NYDJREZIZCVKQZ-UHFFFAOYSA-L [K+].[K+].[K+].P([O-])([O-])=O Chemical compound [K+].[K+].[K+].P([O-])([O-])=O NYDJREZIZCVKQZ-UHFFFAOYSA-L 0.000 claims 1
- 125000003916 ethylene diamine group Chemical group 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- RRBYUSWBLVXTQN-UHFFFAOYSA-N tricyclene Chemical compound C12CC3CC2C1(C)C3(C)C RRBYUSWBLVXTQN-UHFFFAOYSA-N 0.000 claims 1
- RRBYUSWBLVXTQN-VZCHMASFSA-N tricyclene Natural products C([C@@H]12)C3C[C@H]1C2(C)C3(C)C RRBYUSWBLVXTQN-VZCHMASFSA-N 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- 239000007787 solid Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 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 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000000032 diagnostic agent Substances 0.000 description 3
- 229940039227 diagnostic agent Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 2
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 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
- 239000012614 Q-Sepharose Substances 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001298 alcohols 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
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 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
- 239000013522 chelant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- UFZOPKFMKMAWLU-UHFFFAOYSA-N ethoxy(methyl)phosphinic acid Chemical compound CCOP(C)(O)=O UFZOPKFMKMAWLU-UHFFFAOYSA-N 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
- 238000004108 freeze drying Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000002595 magnetic resonance imaging Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000768 polyamine Polymers 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
- 239000011435 rock Substances 0.000 description 1
- KZUNJOHGWZRPMI-AKLPVKDBSA-N samarium-153 Chemical compound [153Sm] KZUNJOHGWZRPMI-AKLPVKDBSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005671 trienes Chemical class 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 (2)
| 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 |
| PCT/US1994/005134 WO1994026753A1 (en) | 1993-05-06 | 1994-05-04 | Process for the preparation of azamacrocylcic or acyclic aminophosphonate ester derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG100193A BG100193A (bg) | 1996-12-31 |
| BG62775B1 true BG62775B1 (bg) | 2000-07-31 |
Family
ID=22066341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG100193A BG62775B1 (bg) | 1993-05-06 | 1995-12-05 | Метод за получаване на азамакроциклични или ациклични аминофосфонатни естерни производни |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US5714604A (es) |
| EP (1) | EP0698029B1 (es) |
| JP (1) | JP3556669B2 (es) |
| KR (1) | KR100311560B1 (es) |
| CN (1) | CN1042537C (es) |
| AP (1) | AP543A (es) |
| AT (1) | ATE172978T1 (es) |
| AU (1) | AU682190B2 (es) |
| BG (1) | BG62775B1 (es) |
| CA (1) | CA2162170C (es) |
| CO (1) | CO4230080A1 (es) |
| CZ (1) | CZ290993B6 (es) |
| DE (1) | DE69414382T2 (es) |
| DK (1) | DK0698029T3 (es) |
| DZ (1) | DZ1777A1 (es) |
| EE (1) | EE03159B1 (es) |
| EG (1) | EG20296A (es) |
| ES (1) | ES2123137T3 (es) |
| FI (1) | FI115632B (es) |
| HK (1) | HK1014537A1 (es) |
| HU (1) | HU223769B1 (es) |
| IL (1) | IL109561A (es) |
| IS (1) | IS1735B (es) |
| LT (1) | LT3713B (es) |
| LV (1) | LV10867B (es) |
| MA (1) | MA23186A1 (es) |
| NO (1) | NO304742B1 (es) |
| PL (1) | PL180756B1 (es) |
| RO (1) | RO115883B1 (es) |
| RU (1) | RU2135507C1 (es) |
| TN (1) | TNSN94040A1 (es) |
| TW (1) | TW273549B (es) |
| UA (1) | UA44704C2 (es) |
| WO (1) | WO1994026753A1 (es) |
| ZA (1) | ZA943158B (es) |
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 |
| AU5375896A (en) * | 1995-03-27 | 1996-10-16 | 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 |
| CA2382877A1 (en) * | 1999-10-18 | 2001-04-26 | Dow Global Technologies Inc. | Aminoalkylenephosphonates for treatment of bone disorders |
| US6794371B1 (en) * | 1999-10-18 | 2004-09-21 | The Dow Chemical Company | Aminoalkylenephosphonates for treatment of bone disorders |
| US6565828B2 (en) * | 2000-04-07 | 2003-05-20 | Bristol-Myers Squibb Company | Macrocyclic chelants for metallopharmaceuticals |
| WO2002062398A2 (en) | 2001-01-08 | 2002-08-15 | Neorx Corporation | Radioactively labelled conjugates of phosphonates |
| WO2003035114A1 (en) * | 2001-10-22 | 2003-05-01 | Dow Global Technologies Inc. | Radiopharmaceutical agent for the treatment of early stage cancer |
| ATE309254T1 (de) * | 2001-10-22 | 2005-11-15 | Univ Texas Tech | Gewebespezifische fluoreszierende chelate |
| 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 |
| WO2006020779A2 (en) * | 2004-08-10 | 2006-02-23 | 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 |
| DE69028001T2 (de) * | 1989-11-27 | 1996-12-19 | Concat Ltd | Qualitätssteigerung von mr-bildern von knochen und ähnlichem gewebe mittels paramagnetischer kationenkomplexe und polyphosphonatliganden |
| 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 EP EP94917333A patent/EP0698029B1/en not_active Expired - Lifetime
- 1994-05-04 JP JP52562094A patent/JP3556669B2/ja not_active Expired - Fee Related
- 1994-05-04 CA CA002162170A patent/CA2162170C/en not_active Expired - Fee Related
- 1994-05-04 PL PL94311651A patent/PL180756B1/pl not_active IP Right Cessation
- 1994-05-04 RO RO95-01927A patent/RO115883B1/ro unknown
- 1994-05-04 DE DE69414382T patent/DE69414382T2/de not_active Expired - Lifetime
- 1994-05-04 WO PCT/US1994/005134 patent/WO1994026753A1/en active IP Right Grant
- 1994-05-04 DK DK94917333T patent/DK0698029T3/da active
- 1994-05-04 KR KR1019950704944A patent/KR100311560B1/ko not_active IP Right Cessation
- 1994-05-04 HU HU9503175A patent/HU223769B1/hu not_active IP Right Cessation
- 1994-05-04 ES ES94917333T patent/ES2123137T3/es not_active Expired - Lifetime
- 1994-05-04 DZ DZ940043A patent/DZ1777A1/fr active
- 1994-05-04 CZ CZ19952890A patent/CZ290993B6/cs not_active IP Right Cessation
- 1994-05-04 CN CN94192530A patent/CN1042537C/zh not_active Expired - Fee Related
- 1994-05-04 AT AT94917333T patent/ATE172978T1/de not_active IP Right Cessation
- 1994-05-04 UA UA95114920A patent/UA44704C2/uk unknown
- 1994-05-04 AU AU69086/94A patent/AU682190B2/en not_active Ceased
- 1994-05-05 MA MA23494A patent/MA23186A1/fr unknown
- 1994-05-05 IS IS4158A patent/IS1735B/is unknown
- 1994-05-05 RU RU95122389A patent/RU2135507C1/ru not_active IP Right Cessation
- 1994-05-05 IL IL10956194A patent/IL109561A/en not_active IP Right Cessation
- 1994-05-06 CO CO94018967A patent/CO4230080A1/es unknown
- 1994-05-06 LT LTIP1925A patent/LT3713B/lt not_active IP Right Cessation
- 1994-05-06 ZA ZA943158A patent/ZA943158B/xx unknown
- 1994-05-06 TN TNTNSN94040A patent/TNSN94040A1/fr unknown
- 1994-05-06 LV LVP-94-99A patent/LV10867B/en unknown
- 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
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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
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1998
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