HUE032290T2 - Eljárások fém-mezoporfirinek elõállítására - Google Patents
Eljárások fém-mezoporfirinek elõállítására Download PDFInfo
- Publication number
- HUE032290T2 HUE032290T2 HUE12765367A HUE12765367A HUE032290T2 HU E032290 T2 HUE032290 T2 HU E032290T2 HU E12765367 A HUE12765367 A HU E12765367A HU E12765367 A HUE12765367 A HU E12765367A HU E032290 T2 HUE032290 T2 HU E032290T2
- Authority
- HU
- Hungary
- Prior art keywords
- tin
- mesoporphyrin
- reaction
- hours
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 60
- 229910052751 metal Inorganic materials 0.000 title description 45
- 239000002184 metal Substances 0.000 title description 45
- 230000002194 synthesizing effect Effects 0.000 title description 13
- 235000019788 craving Nutrition 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 72
- LLDZJTIZVZFNCM-UHFFFAOYSA-J 3-[18-(2-carboxyethyl)-8,13-diethyl-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid;dichlorotin(2+) Chemical compound [H+].[H+].[Cl-].[Cl-].[Sn+4].[N-]1C(C=C2C(=C(C)C(=CC=3C(=C(C)C(=C4)N=3)CC)[N-]2)CCC([O-])=O)=C(CCC([O-])=O)C(C)=C1C=C1C(C)=C(CC)C4=N1 LLDZJTIZVZFNCM-UHFFFAOYSA-J 0.000 description 66
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 66
- 229910052718 tin Inorganic materials 0.000 description 62
- 239000000047 product Substances 0.000 description 52
- NCAJWYASAWUEBY-UHFFFAOYSA-N 3-[20-(2-carboxyethyl)-9,14-diethyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6(24),7,9,11,13,15,17,19-undecaen-4-yl]propanoic acid Chemical compound N1C2=C(C)C(CC)=C1C=C(N1)C(C)=C(CC)C1=CC(C(C)=C1CCC(O)=O)=NC1=CC(C(CCC(O)=O)=C1C)=NC1=C2 NCAJWYASAWUEBY-UHFFFAOYSA-N 0.000 description 51
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
- -1 tin mesoporphyrin compound Chemical class 0.000 description 46
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 42
- BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 description 41
- 229940025294 hemin Drugs 0.000 description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- 229950001307 stannsoporfin Drugs 0.000 description 37
- 239000000543 intermediate Substances 0.000 description 36
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 32
- 238000005984 hydrogenation reaction Methods 0.000 description 32
- 239000003054 catalyst Substances 0.000 description 31
- 229950003776 protoporphyrin Drugs 0.000 description 30
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 21
- 229910001887 tin oxide Inorganic materials 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 19
- 239000000908 ammonium hydroxide Substances 0.000 description 19
- 238000001914 filtration Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 17
- 235000019253 formic acid Nutrition 0.000 description 17
- KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical compound CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 239000001301 oxygen Substances 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 13
- 235000003891 ferrous sulphate Nutrition 0.000 description 12
- 239000011790 ferrous sulphate Substances 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 238000010949 in-process test method Methods 0.000 description 12
- 229910052763 palladium Inorganic materials 0.000 description 12
- 239000000376 reactant Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 238000003780 insertion Methods 0.000 description 11
- 230000037431 insertion Effects 0.000 description 11
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 11
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 11
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 10
- 239000005909 Kieselgur Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 10
- DBOVLDLKDZRBNC-UHFFFAOYSA-J 2,4,6,7,8-pentaoxa-3lambda5,5lambda5-diphospha-1-stannatricyclo[3.1.1.11,3]octane 3,5-dioxide hydrate Chemical compound O.[Sn+4].[O-]P([O-])(=O)OP([O-])([O-])=O DBOVLDLKDZRBNC-UHFFFAOYSA-J 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- PGGZKNHTKRUCJS-UHFFFAOYSA-N methanesulfonic acid;tin Chemical compound [Sn].CS(O)(=O)=O PGGZKNHTKRUCJS-UHFFFAOYSA-N 0.000 description 9
- 230000001590 oxidative effect Effects 0.000 description 9
- FAKFSJNVVCGEEI-UHFFFAOYSA-J tin(4+);disulfate Chemical compound [Sn+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O FAKFSJNVVCGEEI-UHFFFAOYSA-J 0.000 description 9
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 9
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 229910052742 iron Inorganic materials 0.000 description 8
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 7
- LQBPATQBTSBIIH-UHFFFAOYSA-N methyl 3-[8,13-bis(ethenyl)-18-(3-methoxy-3-oxopropyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoate Chemical compound N1C(C=C2C(=C(C=C)C(=CC=3C(=C(CCC(=O)OC)C(=C4)N=3)C)N2)C)=C(C=C)C(C)=C1C=C1C(C)=C(CCC(=O)OC)C4=N1 LQBPATQBTSBIIH-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 5
- 229910052793 cadmium Inorganic materials 0.000 description 5
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 5
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical compound [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 4
- 229910052785 arsenic Inorganic materials 0.000 description 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 229910052733 gallium Inorganic materials 0.000 description 4
- 229910052732 germanium Inorganic materials 0.000 description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000011135 tin Substances 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000006713 insertion reaction Methods 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000004032 porphyrins Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002516 radical scavenger Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000006478 transmetalation reaction Methods 0.000 description 3
- UOCLRXFKRLRMKV-UHFFFAOYSA-N trolnitrate phosphate Chemical compound OP(O)(O)=O.OP(O)(O)=O.[O-][N+](=O)OCCN(CCO[N+]([O-])=O)CCO[N+]([O-])=O UOCLRXFKRLRMKV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- PLONEVHFXDFSLA-UHFFFAOYSA-N ethyl hexanoate;tin(2+) Chemical compound [Sn+2].CCCCCC(=O)OCC PLONEVHFXDFSLA-UHFFFAOYSA-N 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 150000003278 haem Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ZSUXOVNWDZTCFN-UHFFFAOYSA-L tin(ii) bromide Chemical compound Br[Sn]Br ZSUXOVNWDZTCFN-UHFFFAOYSA-L 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- VAJVGAQAYOAJQI-UHFFFAOYSA-N 3-[18-(2-carboxylatoethyl)-3,8,13,17-tetramethyl-22,23-dihydroporphyrin-21,24-diium-2-yl]propanoate Chemical compound N1C(C=C2C(C)=CC(N2)=CC=2C(=C(CCC(O)=O)C(=C3)N=2)C)=CC(C)=C1C=C1C(C)=C(CCC(O)=O)C3=N1 VAJVGAQAYOAJQI-UHFFFAOYSA-N 0.000 description 1
- KFKRXESVMDBTNQ-UHFFFAOYSA-N 3-[18-(2-carboxylatoethyl)-8,13-bis(1-hydroxyethyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-21,24-diium-2-yl]propanoate Chemical class N1C2=C(C)C(C(C)O)=C1C=C(N1)C(C)=C(C(O)C)C1=CC(C(C)=C1CCC(O)=O)=NC1=CC(C(CCC(O)=O)=C1C)=NC1=C2 KFKRXESVMDBTNQ-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- 101001021103 Homo sapiens Oxygen-dependent coproporphyrinogen-III oxidase, mitochondrial Proteins 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
- 206010023126 Jaundice Diseases 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 102100036201 Oxygen-dependent coproporphyrinogen-III oxidase, mitochondrial Human genes 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- AFNRRBXCCXDRPS-UHFFFAOYSA-N tin(ii) sulfide Chemical compound [Sn]=S AFNRRBXCCXDRPS-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2284—Compounds with one or more Sn-N linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (2)
1 #MÄteii&'s &s««!y |«?M«a8^.hwf8 vnssï*smséyH#àsâi és «x ósí·· '1 j.Hàfïifi öfX-:·:ííí ííi VrjyyülA Aöikgä&grA «?ri«:V ;;s$ldm«.Xî:S p;\>î*p<s14 V^-sg:-iSíS:.:r sVéxtiMsàâ #;M feégMséi s p-xüUip«ríi íkí· sí:í;i ! :· óstScíiïc és M%p?|4ykstg5rdn8A^ pkirögákséégéé. J, Αχ |.,ν KSg¥ *. igèkypeîk SxKfííki éljáras, aSöl Ax <&$'UMÀÂSséfc kSAii.sAjíssKíöti: ásAsssíd, AaAksiA áft-ssülISi éB'hmnésI, 'étt“«aláti éiAgéxkésxíÉkkíMk ^l*eiíih«8öMs «íAmeíássxailbfsssv és éfï" kV Alarmévá ssxkkknák
4, Αχ f. vágy é, ígégygAíkíA â&mrsïs öprés/alpíáxSn^^gyöpAVflríRvöéySiéVAséPSé^Vkg,
Applications Claiming Priority (3)
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| US201161469791P | 2011-03-30 | 2011-03-30 | |
| US201161469792P | 2011-03-30 | 2011-03-30 | |
| US201161532301P | 2011-09-08 | 2011-09-08 |
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| HUE032290T2 true HUE032290T2 (hu) | 2017-09-28 |
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| HUE12765367A HUE032290T2 (hu) | 2011-03-30 | 2012-03-30 | Eljárások fém-mezoporfirinek elõállítására |
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| US (5) | US8735574B2 (hu) |
| EP (1) | EP2691398B1 (hu) |
| DK (1) | DK2691398T3 (hu) |
| ES (1) | ES2609110T3 (hu) |
| HU (1) | HUE032290T2 (hu) |
| PL (1) | PL2691398T3 (hu) |
| PT (1) | PT2691398T (hu) |
| WO (1) | WO2012135686A1 (hu) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2556359T3 (es) | 2006-10-04 | 2016-01-15 | Infacare Pharmaceutical Corporation | Procedimiento para la producción a gran escala de estansoporfina de alta pureza |
| EP2691398B1 (en) | 2011-03-30 | 2016-09-28 | InfaCare Pharmaceutical Corporation | Methods for synthesizing metal mesoporphyrins |
| KR20160094385A (ko) | 2013-12-05 | 2016-08-09 | 허니웰 인터내셔날 인코포레이티드 | 조절된 pH를 갖는 주석(II) 메탄술포네이트 용액 |
| CN106536609B (zh) | 2014-07-07 | 2022-04-29 | 霍尼韦尔国际公司 | 具有离子清除剂的热界面材料 |
| IL287607B (en) | 2014-09-29 | 2022-07-01 | Hutchinson Fred Cancer Res | Preparations, kits and methods for inducing acquired cellular resistance using induced stress proteins |
| EP3227399B1 (en) | 2014-12-05 | 2021-07-14 | Honeywell International Inc. | High performance thermal interface materials with low thermal impedance |
| US10312177B2 (en) | 2015-11-17 | 2019-06-04 | Honeywell International Inc. | Thermal interface materials including a coloring agent |
| US10781349B2 (en) | 2016-03-08 | 2020-09-22 | Honeywell International Inc. | Thermal interface material including crosslinker and multiple fillers |
| US10501671B2 (en) | 2016-07-26 | 2019-12-10 | Honeywell International Inc. | Gel-type thermal interface material |
| US11041103B2 (en) | 2017-09-08 | 2021-06-22 | Honeywell International Inc. | Silicone-free thermal gel |
| US10428256B2 (en) | 2017-10-23 | 2019-10-01 | Honeywell International Inc. | Releasable thermal gel |
| US11072706B2 (en) | 2018-02-15 | 2021-07-27 | Honeywell International Inc. | Gel-type thermal interface material |
| US11373921B2 (en) | 2019-04-23 | 2022-06-28 | Honeywell International Inc. | Gel-type thermal interface material with low pre-curing viscosity and elastic properties post-curing |
| AU2021355498A1 (en) * | 2020-10-02 | 2023-05-18 | Adgero Biopharmaceuticals Holdings, Inc. | Methods for the production of nickel (ii) etioporphyrin-i |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4684637A (en) | 1981-07-15 | 1987-08-04 | The Rockefeller University | Method of decreasing rate of heme metabolism |
| JPS58501130A (ja) | 1981-07-15 | 1983-07-14 | ザ ロツクフエラ− ユニバ−シテイ | ヘムの代謝速度の低下方法 |
| US4708964A (en) | 1984-02-09 | 1987-11-24 | Chemex Pharmaceuticals | Lipoxygenase inhibitors |
| AU570143B2 (en) | 1985-01-14 | 1988-03-03 | Rockefeller University, The | Method of increasing heme excretion from a mammal using tin protoporphyrin |
| US4619923A (en) | 1985-01-14 | 1986-10-28 | The Rockefeller University | Metal protoporphyrins in the control of tryptophan metabolism |
| US4657902A (en) | 1985-03-25 | 1987-04-14 | The Rockefeller University | Therapeutic use of tin mesoporphyrin |
| US4692440A (en) | 1985-03-25 | 1987-09-08 | The Rockefeller University | Therapeutic use of tin mesoporphyrin |
| US4692439A (en) | 1986-06-20 | 1987-09-08 | The Rockefeller University | Therapeutic use of tin diiododeuteroporphyrin |
| US4668670A (en) | 1986-06-20 | 1987-05-26 | The Rockefeller University | Tin diiododeuteroporphyrin and therapeutic use thereof |
| US4861876A (en) | 1986-11-26 | 1989-08-29 | Wayne State University | Hematoporphyrin derivative and method of preparation and purification |
| US4782049A (en) | 1986-12-08 | 1988-11-01 | The Rockefeller University | Tin protoporphyrin and tin mesoporphyrin in the treatment of psoriasis |
| US4900871A (en) | 1987-01-02 | 1990-02-13 | Sun Refining And Marketing Company | Hydrocarbon oxidations catalyzed by iron coordination complexes containing a halogenated ligand |
| US5990363A (en) | 1987-01-02 | 1999-11-23 | Sun Company, Inc. | Method for oxidizing alkanes using novel porphyrins synthesized from dipyrromethanes and aldehydes |
| AU603938B2 (en) | 1987-09-08 | 1990-11-29 | Rockefeller University, The | Use of metalloporphyrins to reverse the toxic effect of tumor therapy |
| US5081115A (en) | 1987-10-15 | 1992-01-14 | The Board Of Trustees Of The Leland Stanford Junior University | Method to prevent neonatal jaundice with metalloporphyrin compositions |
| US4831024A (en) | 1987-10-15 | 1989-05-16 | The Board Of Trustees Of The Leland Stanford Junior University | Method to prevent neonatal jaundice |
| DE3827940A1 (de) | 1988-08-13 | 1990-03-01 | Schering Ag | 13,17-propionsaeure- und propionsaeurederivat- substituierte porphyrin-komplexverbindungen, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| US5162313A (en) | 1989-03-16 | 1992-11-10 | The Rockefeller University | Control of heme and iron concentrations in body tissues |
| US5223494A (en) | 1989-09-25 | 1993-06-29 | The Rockefeller University | Orally administered porphyrins to control intestinal iron absorption |
| US5062775A (en) | 1989-09-29 | 1991-11-05 | Rocky Mountain Research, Inc. | Roller pump in an extra corporeal support system |
| US5010073A (en) | 1989-10-05 | 1991-04-23 | The Rockefeller University | Use of liposomes as carriers for metalloporphyrins |
| US5192757A (en) | 1990-12-20 | 1993-03-09 | Glaxo Inc. | Cobalt porphyrins |
| AU2401992A (en) | 1991-08-01 | 1993-03-02 | E.I. Du Pont De Nemours And Company | Herbicidal quinoxalinyloxy ethers |
| US5493017A (en) | 1992-08-14 | 1996-02-20 | The Trustees Of The University Of Pennsylvania | Ring-metalated porphyrins |
| US5371199B1 (en) | 1992-08-14 | 1995-12-26 | Univ Pennsylvania | Substituted porphyrins porphyrin-containing polymers and synthetic methods therefor |
| US5817830A (en) | 1992-08-14 | 1998-10-06 | Trustees Of The University Of Pennsylvania | Pyrrolic compounds |
| WO1994028906A1 (en) | 1993-06-14 | 1994-12-22 | The Rockefeller University | Treatment of neonatal hyperbilirubin with metalloporphyrin |
| US5665869A (en) * | 1993-11-15 | 1997-09-09 | Somatogen, Inc. | Method for the rapid removal of protoporphyrin from protoporphyrin IX-containing solutions of hemoglobin |
| CA2130853A1 (en) | 1994-08-25 | 1996-02-26 | Svetlana Kudrevich | Process for the syntheses of monosulphonated phthalocyanines, naphthobenzoporphyrazines and porphyrins via a modified meerwein reaction |
| US6066333A (en) | 1994-09-22 | 2000-05-23 | William Harvey Research Limited | Pharmaceutical control of inflammation |
| US5912341A (en) | 1995-03-14 | 1999-06-15 | Hoffman/Barrett, L.L.C. | Heteroatom-functionalized porphyrazines and multimetallic complexes and polymers derived therefrom |
| AU6497996A (en) | 1995-08-02 | 1997-02-26 | Warner-Lambert Company | Amino acid complexes of cobalt (iii) mesoporphyrin ix and cobalt (iii) protoporphyrin ix |
| US5883246A (en) | 1996-03-07 | 1999-03-16 | Qlt Phototherapeutics, Inc. | Synthesis of polypyrrolic macrocycles from meso-substituted tripyrrane compounds |
| US6004530A (en) | 1996-06-04 | 1999-12-21 | Roche Diagnostics Gmbh | Use of metallo-porphyrin conjugates for the detection of biological substances |
| GB9616353D0 (en) | 1996-08-03 | 1996-09-11 | Secr Defence | Metallo-porphyrins |
| US6124452A (en) | 1997-12-19 | 2000-09-26 | University Of Nebraska-Lincoln | Octafluoro-meso-tetraarylporphyrins and methods for making these compounds |
| DE19706490C1 (de) | 1997-02-19 | 1998-09-17 | Deutsches Krebsforsch | Verfahren zur Herstellung von Säureamiden und zur Metallierung von Verbindungen und Verwendung der nach den Verfahren hergestellten Verbindungen |
| US5886173A (en) | 1997-07-30 | 1999-03-23 | Pharmacyclics, Inc. | Metallation of macrocycles with 2,4-dicarbonyl-metal complexes |
| US6194566B1 (en) | 1997-12-02 | 2001-02-27 | Schering Aktiengesellschaft | Process for the production of metalloporphyrin-metal complex conjugates |
| JP3673888B2 (ja) | 1998-03-09 | 2005-07-20 | 独立行政法人科学技術振興機構 | ポルフィリン類金属錯体の製造方法 |
| DE19831217A1 (de) | 1998-07-03 | 2000-01-05 | Schering Ag | Neue Porphyrinderivate, diese enthaltende pharmazeutische Mittel und ihre Verwendung in der photodynamischen Therapie und MRI-Diagnostik |
| US5973141A (en) | 1998-11-27 | 1999-10-26 | Miravant Pharmaceuticals, Inc. | Method for the demethoxycarbonylation of porphyrinic compounds such as pheophorbides |
| AU2001243578A1 (en) | 2000-03-10 | 2001-09-24 | The Rockefeller University | Modulation of cardiovascular injury |
| US6462192B2 (en) | 2001-01-23 | 2002-10-08 | Miravant Pharmaceuticals, Inc. | Processes for large scale production of tetrapyrroles |
| US6906050B2 (en) | 2001-05-31 | 2005-06-14 | Miravant Pharmaceuticals, Inc. | Substituted porphyrin and azaporphyrin derivatives and their use in photodynamic therapy, radioimaging and MRI diagnosis |
| US7375216B2 (en) | 2002-06-04 | 2008-05-20 | Infacare Pharmaceutical Corporation | Preparation of metal mesoporphyrin compounds |
| EP2270016A1 (en) | 2002-06-04 | 2011-01-05 | InfaCare Pharmaceutical Corporation | Preparation of metal mesoporphyrin halide compounds |
| US7157401B2 (en) | 2002-10-17 | 2007-01-02 | Carnegie Mellon University | Catalyst for the treatment of organic compounds |
| US20040097481A1 (en) * | 2002-11-20 | 2004-05-20 | Benjamin Levinson | Water-soluble mesoporphyrin compounds and methods of preparation |
| JP2006515882A (ja) | 2003-01-08 | 2006-06-08 | カイロン コーポレイション | 組織因子経路インヒビター（ｔｆｐｉ）または組織因子経路インヒビター改変体を含有する安定化水性組成物 |
| NL1025049C2 (nl) | 2003-12-18 | 2005-06-21 | Photobiochem N V | Werkwijze voor de bereiding van porfyrinederivaten. |
| US20060222668A1 (en) | 2005-04-01 | 2006-10-05 | Wellspring Pharmaceutical Corporation | Stannsoporfin compositions, drug products and methods of manufacture |
| EP1865777A4 (en) | 2005-04-01 | 2008-07-16 | Infacare Pharmaceutical Corp | STANNSOPORFIN COMPOSITIONS AND ADMINISTRATION |
| AU2012202684B2 (en) | 2006-10-04 | 2014-04-10 | Mallinckrodt Hospital Products IP Limited | High-purity large-scale preparation of stannsoporfin |
| US20080113955A1 (en) | 2006-10-04 | 2008-05-15 | Benjamin Levinson | Treatment of infant hyperbilirubinemia using low dosages of stannsoporfin |
| ES2369876T3 (es) | 2006-10-04 | 2011-12-07 | Infacare Pharmaceutical Corporation | Procedimiento para la producción a gran escala de estansoporfina de alta pureza. |
| ES2556359T3 (es) | 2006-10-04 | 2016-01-15 | Infacare Pharmaceutical Corporation | Procedimiento para la producción a gran escala de estansoporfina de alta pureza |
| FR2914302A1 (fr) | 2007-03-30 | 2008-10-03 | Sanofi Pasteur Sa | Procede de preparation de derives de porphyrine, telle que la protoporphyrine (ix) et intermediaire de synthese |
| EP2691398B1 (en) | 2011-03-30 | 2016-09-28 | InfaCare Pharmaceutical Corporation | Methods for synthesizing metal mesoporphyrins |
| EP2788002A4 (en) | 2011-12-01 | 2015-06-03 | Infacare Pharmaceutical Corp | METHOD FOR THE TREATMENT OF HYPERBILIRUBINEMIA WITH STANPSOPORFIN |
-
2012
- 2012-03-30 EP EP12765367.3A patent/EP2691398B1/en active Active
- 2012-03-30 HU HUE12765367A patent/HUE032290T2/hu unknown
- 2012-03-30 PL PL12765367T patent/PL2691398T3/pl unknown
- 2012-03-30 DK DK12765367.3T patent/DK2691398T3/en active
- 2012-03-30 US US13/435,868 patent/US8735574B2/en active Active
- 2012-03-30 ES ES12765367.3T patent/ES2609110T3/es active Active
- 2012-03-30 PT PT127653673T patent/PT2691398T/pt unknown
- 2012-03-30 WO PCT/US2012/031557 patent/WO2012135686A1/en active Application Filing
-
2014
- 2014-04-15 US US14/253,710 patent/US9181285B2/en not_active Expired - Fee Related
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2015
- 2015-10-05 US US14/875,141 patent/US9688705B2/en active Active
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2017
- 2017-05-24 US US15/603,654 patent/US20170260217A1/en not_active Abandoned
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2018
- 2018-09-07 US US16/125,190 patent/US10533024B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20190002481A1 (en) | 2019-01-03 |
| US9688705B2 (en) | 2017-06-27 |
| US20170260217A1 (en) | 2017-09-14 |
| EP2691398A1 (en) | 2014-02-05 |
| EP2691398A4 (en) | 2014-10-08 |
| US9181285B2 (en) | 2015-11-10 |
| ES2609110T3 (es) | 2017-04-18 |
| WO2012135686A1 (en) | 2012-10-04 |
| PL2691398T3 (pl) | 2017-07-31 |
| PT2691398T (pt) | 2017-01-02 |
| US20160024124A1 (en) | 2016-01-28 |
| US10533024B2 (en) | 2020-01-14 |
| US20120253033A1 (en) | 2012-10-04 |
| US8735574B2 (en) | 2014-05-27 |
| DK2691398T3 (en) | 2017-01-16 |
| EP2691398B1 (en) | 2016-09-28 |
| US20140228560A1 (en) | 2014-08-14 |
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