JP4939398B2 - 金属メソポルフィリンハライド化合物の調製 - Google Patents
金属メソポルフィリンハライド化合物の調製 Download PDFInfo
- Publication number
- JP4939398B2 JP4939398B2 JP2007506137A JP2007506137A JP4939398B2 JP 4939398 B2 JP4939398 B2 JP 4939398B2 JP 2007506137 A JP2007506137 A JP 2007506137A JP 2007506137 A JP2007506137 A JP 2007506137A JP 4939398 B2 JP4939398 B2 JP 4939398B2
- Authority
- JP
- Japan
- Prior art keywords
- mesoporphyrin
- metal
- halide
- formate
- tin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229910052751 metal Inorganic materials 0.000 title claims description 64
- 239000002184 metal Substances 0.000 title claims description 64
- -1 mesoporphyrin halide compounds Chemical class 0.000 title claims description 49
- 238000002360 preparation method Methods 0.000 title description 7
- 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 claims description 92
- 238000000034 method Methods 0.000 claims description 55
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 48
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 47
- 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 claims description 39
- 239000011541 reaction mixture Substances 0.000 claims description 26
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 24
- 235000019253 formic acid Nutrition 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 24
- 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 claims description 22
- 229940025294 hemin Drugs 0.000 claims description 22
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical group [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 claims description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 18
- 229950001307 stannsoporfin Drugs 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000002516 radical scavenger Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 229910052718 tin Inorganic materials 0.000 claims description 8
- 239000011135 tin Substances 0.000 claims description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 238000003780 insertion Methods 0.000 claims description 6
- 230000037431 insertion Effects 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000003610 charcoal Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 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 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
- 238000003756 stirring Methods 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 52
- 239000000725 suspension Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000012065 filter cake Substances 0.000 description 35
- 239000000047 product Substances 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 239000000543 intermediate Substances 0.000 description 28
- 239000000706 filtrate Substances 0.000 description 20
- 239000008213 purified water Substances 0.000 description 19
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 239000000908 ammonium hydroxide Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000001914 filtration Methods 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 10
- 229920004933 Terylene® Polymers 0.000 description 10
- 239000004744 fabric Substances 0.000 description 10
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 10
- 239000005020 polyethylene terephthalate Substances 0.000 description 10
- 238000010926 purge Methods 0.000 description 10
- 238000000746 purification Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- 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 4
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 229950003776 protoporphyrin Drugs 0.000 description 4
- 235000011150 stannous chloride Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005273 aeration Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 238000011031 large-scale manufacturing process Methods 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 150000004032 porphyrins Chemical group 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000003278 haem Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000004237 preparative chromatography Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- 238000005406 washing Methods 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 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
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- 229910001509 metal bromide Inorganic materials 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Images
Classifications
-
- 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
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- 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
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/812,156 | 2004-03-29 | ||
| US10/812,156 US7375216B2 (en) | 2002-06-04 | 2004-03-29 | Preparation of metal mesoporphyrin compounds |
| PCT/US2004/039240 WO2005103056A2 (en) | 2004-03-29 | 2004-11-24 | Preparation of metal mesoporphyrin halide compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007530676A JP2007530676A (ja) | 2007-11-01 |
| JP2007530676A5 JP2007530676A5 (https=) | 2008-01-10 |
| JP4939398B2 true JP4939398B2 (ja) | 2012-05-23 |
Family
ID=35197536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007506137A Expired - Fee Related JP4939398B2 (ja) | 2004-03-29 | 2004-11-24 | 金属メソポルフィリンハライド化合物の調製 |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US7375216B2 (https=) |
| EP (1) | EP1730150A4 (https=) |
| JP (1) | JP4939398B2 (https=) |
| CA (1) | CA2561487C (https=) |
| WO (1) | WO2005103056A2 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8530458B2 (en) | 2006-10-04 | 2013-09-10 | Infacare Pharmaceutical Corporation | High-purity large-scale preparation of stannsoporfin |
| US8735574B2 (en) | 2011-03-30 | 2014-05-27 | Infacare Pharmaceutical Corporation | Methods for synthesizing metal mesoporphyrins |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7375216B2 (en) * | 2002-06-04 | 2008-05-20 | Infacare Pharmaceutical Corporation | Preparation of metal mesoporphyrin compounds |
| GB2397067B (en) | 2002-12-23 | 2005-05-11 | Destiny Pharma Ltd | Porphin & azaporphin derivatives with at least one cationic-nitrogen-containing meso-substituent for use in photodynamic therapy & in vitro sterilisation |
| GB2415372A (en) | 2004-06-23 | 2005-12-28 | Destiny Pharma Ltd | Non photodynamical or sonodynamical antimicrobial use of porphyrins and azaporphyrins containing at least one cationic-nitrogen-containing substituent |
| 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 |
| US20070077480A1 (en) * | 2005-10-05 | 2007-04-05 | Curello Andrew J | Scavenger materials in fuel cartridge |
| US20080113955A1 (en) * | 2006-10-04 | 2008-05-15 | Benjamin Levinson | Treatment of infant hyperbilirubinemia using low dosages of stannsoporfin |
| IT1403087B1 (it) * | 2010-11-05 | 2013-10-04 | Lombardi | Catalizzatori ad alta efficienza, loro preparazione e uso |
| AU2012345646A1 (en) | 2011-12-01 | 2014-06-26 | Infacare Pharmaceutical Corporation | Methods for treating hyperbilirubinemia with stannsoporfin |
| CN103193783A (zh) * | 2013-03-29 | 2013-07-10 | 甘肃农业大学 | 一种以牦牛血粉为原料制备氯化血红素的方法 |
| SI3200582T1 (sl) | 2014-09-29 | 2024-04-30 | Fred Hutchinson Cancer Center | Sestave, kompleti in metode za indukcijo pridobljene citorezistence z uporabo induktorjev stresnih proteinov |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003101999A2 (en) * | 2002-06-04 | 2003-12-11 | Wellspring Pharmaceutical Corporation | Preparation of metal mesoporphyrin halide compounds |
Family Cites Families (50)
| 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 |
| WO1989002269A1 (en) | 1987-09-08 | 1989-03-23 | The Rockefeller University | 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 |
| 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 |
| 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 |
| WO1997005152A1 (en) | 1995-08-02 | 1997-02-13 | 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 |
| JP2003526668A (ja) | 2000-03-10 | 2003-09-09 | ザ ロックフェラー ユニバーシティー | 心臓血管損傷の調節 |
| US6462192B2 (en) * | 2001-01-23 | 2002-10-08 | Miravant Pharmaceuticals, Inc. | Processes for large scale production of tetrapyrroles |
| CA2448570A1 (en) | 2001-05-31 | 2002-12-05 | 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 |
| US20040097481A1 (en) | 2002-11-20 | 2004-05-20 | Benjamin Levinson | Water-soluble mesoporphyrin compounds and methods of preparation |
| DE602004019761D1 (de) * | 2003-01-08 | 2009-04-16 | Novartis Vaccines & Diagnostic | Stabilisierte wässrige zusammensetzungen mit gewebefaktorinhibitor (tfpi) oder gewebefaktorinhibitor-variante |
| EP1865777A4 (en) | 2005-04-01 | 2008-07-16 | Infacare Pharmaceutical Corp | STANNSOPORFIN COMPOSITIONS AND ADMINISTRATION |
| US20060222668A1 (en) * | 2005-04-01 | 2006-10-05 | Wellspring Pharmaceutical Corporation | Stannsoporfin compositions, drug products and methods of manufacture |
| US20080113955A1 (en) * | 2006-10-04 | 2008-05-15 | Benjamin Levinson | Treatment of infant hyperbilirubinemia using low dosages of stannsoporfin |
| US7960371B2 (en) * | 2006-10-04 | 2011-06-14 | Infacare Pharmaceutical Corporation | High-purity large-scale preparation of stannsoporfin |
-
2004
- 2004-03-29 US US10/812,156 patent/US7375216B2/en not_active Expired - Lifetime
- 2004-11-24 EP EP04811883A patent/EP1730150A4/en not_active Withdrawn
- 2004-11-24 CA CA2561487A patent/CA2561487C/en not_active Expired - Lifetime
- 2004-11-24 JP JP2007506137A patent/JP4939398B2/ja not_active Expired - Fee Related
- 2004-11-24 WO PCT/US2004/039240 patent/WO2005103056A2/en not_active Ceased
-
2007
- 2007-12-14 US US11/957,317 patent/US7777028B2/en not_active Expired - Lifetime
-
2010
- 2010-07-09 US US12/833,873 patent/US8178664B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003101999A2 (en) * | 2002-06-04 | 2003-12-11 | Wellspring Pharmaceutical Corporation | Preparation of metal mesoporphyrin halide compounds |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8530458B2 (en) | 2006-10-04 | 2013-09-10 | Infacare Pharmaceutical Corporation | High-purity large-scale preparation of stannsoporfin |
| US8835416B2 (en) | 2006-10-04 | 2014-09-16 | Infacare Pharmaceutical Corporation | High-purity large-scale preparation of stannsoporfin |
| US9107927B2 (en) | 2006-10-04 | 2015-08-18 | Infacare Pharmaceutical Corporation | High-purity large-scale preparation of stannsoporfin |
| US9517239B2 (en) | 2006-10-04 | 2016-12-13 | Infacare Pharmaceutical Corporation | High-purity large-scale preparation of stannsoporfin |
| US9902745B2 (en) | 2006-10-04 | 2018-02-27 | Infacare Pharmaceutical Corporation | High-purity large-scale preparation of stannsoporfin |
| US10273255B2 (en) | 2006-10-04 | 2019-04-30 | Infacare Pharmaceutical Corporation | High-purity large-scale preparation of stannsoporfin |
| US10662209B2 (en) | 2006-10-04 | 2020-05-26 | Mallinckrodt Hospital Products IP Limited | High-purity large-scale preparation of stannsoporfin |
| US11078220B2 (en) | 2006-10-04 | 2021-08-03 | Mallinckrodt Hospital Products IP Limited | High-purity large-scale preparation of stannsoporfin |
| US8735574B2 (en) | 2011-03-30 | 2014-05-27 | Infacare Pharmaceutical Corporation | Methods for synthesizing metal mesoporphyrins |
| US9181285B2 (en) | 2011-03-30 | 2015-11-10 | Infacare Pharmaceutical Corporation | Methods for synthesizing metal mesoporphyrins |
| US9688705B2 (en) | 2011-03-30 | 2017-06-27 | Infacare Pharmaceutical Corporation | Methods for synthesizing metal mesoporphyrins |
| US10533024B2 (en) | 2011-03-30 | 2020-01-14 | Mallinckrodt Hosptial Products Ip Limited | Methods for synthesizing metal mesoporphyrins |
Also Published As
| Publication number | Publication date |
|---|---|
| US7777028B2 (en) | 2010-08-17 |
| US8178664B2 (en) | 2012-05-15 |
| EP1730150A2 (en) | 2006-12-13 |
| EP1730150A4 (en) | 2011-05-04 |
| JP2007530676A (ja) | 2007-11-01 |
| WO2005103056A3 (en) | 2007-05-10 |
| WO2005103056A2 (en) | 2005-11-03 |
| CA2561487C (en) | 2012-05-01 |
| US20040210048A1 (en) | 2004-10-21 |
| US20080154033A1 (en) | 2008-06-26 |
| CA2561487A1 (en) | 2005-11-03 |
| US20100280237A1 (en) | 2010-11-04 |
| US7375216B2 (en) | 2008-05-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8178664B2 (en) | Preparation of metal mesoporphyrin compounds | |
| JP5934404B2 (ja) | ジアミノフェノチアジニウム化合物の調製方法 | |
| US10533024B2 (en) | Methods for synthesizing metal mesoporphyrins | |
| JP4309839B2 (ja) | 金属メソポルフィリンハライド化合物の調製 | |
| JPH06271519A (ja) | 5−アミノレブリン酸の製造方法 | |
| CZ18597A3 (en) | Process for preparing 5-amino-2,4,6-triiodine-1,3-benzenedicarboxylic acid | |
| HK1149559A (en) | Preparation of metal mesoporphyrin halide compounds | |
| JPH0892179A (ja) | 5−アミノレブリン酸の製造方法 | |
| CN117820136A (zh) | 2-(2-(2-氨基乙氧基)乙氧基)乙酸的合成方法 | |
| JP2018127406A (ja) | 高純度ブロナンセリンの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20071018 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20071019 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20071019 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20071018 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20101214 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110304 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110311 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110414 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120203 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120224 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150302 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |